Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

doi:10.6023/A21080391

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (11): 1345-1359.DOI: 10.6023/A21080391 Previous Articles Next Articles

Review

不对称Petasis反应在手性胺类化合物合成中的应用

李翼^b, 徐明华^a^,^b^,^*()

a 南方科技大学化学系/深圳格拉布斯研究院广东省催化化学重点实验室深圳 518055
b 中国科学院上海药物研究所新药研究国家重点实验室上海 201203

投稿日期:2021-08-21 发布日期:2021-09-24
通讯作者: 徐明华

作者简介:

李翼, 2009年毕业于武汉大学, 获理学学士学位; 2014年毕业于中国科学院上海药物研究所, 获理学博士学位(导师: 徐明华研究员); 同年留所工作, 任助理研究员. 2016~2018年, 入选上海药明康德“青年人才计划”, 在国内新药研发部担任药物化学项目负责人, 主持创新药物研发项目, 全面负责小分子药物的临床前研究、开发及临床申报工作. 2018年至今, 在美国得克萨斯大学医学分部从事博士后研究. 主要研究兴趣包括不对称合成方法学, 以及针对肿瘤和糖尿病等重大疾病的创新药物研究.

徐明华, 南方科技大学化学系教授. 1999年博士毕业于中国科学院上海有机化学研究所, 先后在美国弗吉尼亚大学和乔治敦大学医学研究中心从事博士后研究; 曾任中国科学院上海药物研究所研究员、课题组长、博士生导师. 主要从事有机不对称合成及手性药物方面的研究, 致力于以一些重要有机分子及药物分子合成为导向的手性化学和手性技术探索, 发展高效不对称催化方法. 中国科学院“百人计划”、国家杰出青年科学基金获得者, 2016年获国家自然科学二等奖.

基金资助:
项目受国家自然科学基金(21971103); 广东省催化化学重点实验室(2020B121201002)

Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

Yi Li^b, Ming-Hua Xu^a^,^b()

a Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China
b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Received:2021-08-21 Published:2021-09-24
Contact: Ming-Hua Xu
Supported by:
National Natural Science Foundation of China(21971103); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

Chiral amines are valuable constituents of many natural products, pharmaceuticals and functional materials, they are also widely utilized as versatile building blocks and important chiral catalysts as well as chiral auxiliaries in organic synthesis. Therefore, it is of great scientific significance and application value to develop efficient methods for the synthesis of structurally diverse chiral amines and chiral amine scaffolds. In 1993, Petasis and co-workers reported an efficient synthesis of allylic amines through a Mannich-type reaction of vinylboronic acids with secondary amines and paraformaldehyde, where the organoboron reagents served as the nucleophilic component. Since then, this three-component Petasis reaction of organoboron reagents with amines and carbonyl derivatives has been developed as an appealing and concise method to access various amines. The asymmetric Petasis reaction provides a facile and efficient route to optically active amines and thus has attracted much attention over the past two decades. In this review, we summarize the recent progress achieved in the synthesis of chiral amines by asymmetric Petasis reaction and provide an overview on the methods applied for stereochemical control. The strategies that have been employed for accessing enantioenriched amines, including various chiral substrate-based diastereoselective induction approaches and several recent developments of enantioselective catalysis. In a large number of asymmetric Petasis reaction cases, good to high levels of stereoselectivities can be achieved relying on the utilization of chiral amine source, chiral carbonyl substrates, and chiral organoboron reagents. In particular, chiral amines such as α-methylbenzylamines and chiral α-hydroxy aldehyde analogues have emerged as a broadly applicable class of substrates for asymmetric Petasis reaction. The most promising advance has been the success of catalytic asymmetric Petasis reaction for enantioselective synthesis of chiral amines in the last few years. Chiral bifunctional thioureas and binaphthols have been demonstrated to be effective organocatalysts. Finally, the perspectives on the relevant challenges and future directions in this field are also discussed.

Key words: Petasis reaction, chiral amine, boronic acid, asymmetric synthesis, asymmetric catalysis

Cite this article

Yi Li, Ming-Hua Xu. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines[J]. Acta Chimica Sinica, 2021, 79(11): 1345-1359.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 51

Figure 1. Petasis reaction

Figure 2. Mechanism of Petasis reaction

Figure 3. Synthesis of β,γ-vinyl-α-amino acid by Petasis reaction

Figure 4. Synthesis of β,γ-vinyl-α-amino acid by asymmetric Petasis reaction

Figure 5. Removal of the amine protecting group by Pd-catalyzed hydrogenation

Figure 6. Synthesis of α-arylglycine derivative by asymmetric Petasis reaction

Figure 7. Chiral α-methylbenzylamine-induced asymmetric Petasis reaction

Figure 8. Asymmetric Petasis reaction of boron ester

Figure 9. (S)-2-phenylglycinol-induced asymmetric Petasis reaction

Figure 10. (S)-2-Phenylglycinol-induced asymmetric Petasis reaction

Figure 11. Asymmetric Petasis reaction of indole-3-boronic acid

Figure 12. Chiral propargylamine-induced asymmetric Petasis reaction

Figure 13. Chiral amino phosphonate-induced asymmetric Petasis reaction

Figure 14. The synthesis of cyclic amino ester via asymmetric Petasis/ RCM reaction

Figure 15. Asymmetric Petasis reaction of allylboronic acid with isatin

Figure 16. Asymmetric Petasis reaction of allylboronic acid ester

Figure 17. Asymmetric Petasis reaction of isoprenylboronates and allenylboronates

Figure 18. Chiral cyclohexane-1,2-diamine-induced asymmetric Petasis reaction

Figure 19. Chiral tert-butanesulfinamide-induced asymmetric Petasis reaction

Figure 20. Synthetic applicability of chiral β,γ-vinyl-α-amino acid derivatives

Figure 21. InBr3-induced asymmetric Petasis reaction of chiral tert-butanesulfinamide

Figure 22. Synthetic applicability of chiral β,γ-vinyl-α-amino acid derivatives

Figure 23. Mechanistic proposals for stereocontrol

Figure 24. Asymmetric Petasis reaction of heteroaryl boronic acid and chiral tert-butanesulfinamide

Figure 25. Asymmetric Petasis reaction of chiral cyclic amino alcohol

Figure 26. Asymmetric Petasis reaction of chiral threonine derivatives

Figure 27. Asymmetric Petasis reaction of chiral lactic acid derivatives and primary amines

Figure 28. Asymmetric Petasis reaction of chiral lactic acid derivatives and secondary amines

Figure 29. BF3-induced asymmetric Petasis reaction

Figure 30. Asymmetric Petasis reaction of chiral α-hydroxyl aldehyde

Figure 31. Asymmetric Petasis reaction of α-hydroxyl aldehyde and allylamine

Figure 32. Asymmetric Petasis reaction of chiral lactol derivatives

Figure 33. Asymmetric Petasis reaction of chiral carbohydrate

Figure 34. Asymmetric Petasis reaction of chiral lactic acid derivatives and allenylboronate

Figure 35. Asymmetric Petasis reaction of chiral α-hydroxyl aldehyde derivatives and allenylboronate

Figure 36. Four components asymmetric Petasis reaction

Figure 37. Asymmetric Petasis reaction of chiral α-amino aldehyde derivatives

Figure 38. Asymmetric Petasis reaction of chiral aziridine aldehyde dimers

Figure 39. Asymmetric Petasis reaction of chiral α-fluorine substituted aldehyde

Figure 40. Chiral (E)-styryl boron ester-induced asymmetric Petasis reaction

Figure 41. Asymmetric Petasis reaction of chiral boron ester and chiral methylbenzylamine

Figure 42. Chiral boronic acid-induced asymmetric Petasis reaction

Figure 43. Chiral thiourea-catalyzed asymmetric Petasis reaction

Figure 44. Chiral thiourea-catalyzed asymmetric Petasis reaction

Figure 45. (S)-VAPOL-catalyzed asymmetric Petasis reaction

Figure 46. The pathway of (S)-VAPOL-catalyzed asymmetric Petasis reaction

Figure 47. Chiral bipheol-catalyzed asymmetric Petasis reaction

Figure 48. Chiral bipheol-catalyzed asymmetric Petasis reaction

Figure 49. Chiral thiourea-bipheol-catalyzed asymmetric Petasis reaction

Figure 50. Chiral bipheol-catalyzed asymmetric Petasis reaction of salicylaldehyde

Figure 51. Proposed mechanism of chiral bipheol-catalyzed asymmetric Petasis reaction of salicylaldehyde

References 51

[1]	(a) Kobayashi S.; Ishitani H. Chem. Rev. 1999, 99, 1069. pmid: 11749440
	(b) Ellman J. A.; Owens T. D.; Tang T. P. Acc. Chem. Res. 2002, 35, 984. doi: 10.1021/ar020066u pmid: 11749440
	(c) Blaser H.-U.; Malan C.; Pugin B.; Spindler F.; Steiner H.; Studer M. Adv. Synth. Catal. 2003, 345, 103. doi: 10.1002/adsc.200390000 pmid: 11749440
	(d) Ellman J. A. Pure Appl. Chem. 2003, 75, 39. doi: 10.1351/pac200375010039 pmid: 11749440
	(e) Kukula P.; Prins R. Top. Catal. 2003, 25, 29. doi: 10.1023/B:TOCA.0000003096.11191.25 pmid: 11749440
	(f) Morton D.; Stockman R. A. Tetrahedron 2006, 62, 8869. doi: 10.1016/j.tet.2006.06.107 pmid: 11749440
	(g) Ramachandran P. V.; Burghardt T. E. Pure Appl. Chem. 2006, 78, 1397. doi: 10.1351/pac200678071397 pmid: 11749440
	(h) Skucas E.; Ngai M.-Y.; Komanduri V.; Krische M. J. Acc. Chem. Res. 2007, 40, 1394. doi: 10.1021/ar7001123 pmid: 11749440
	(i) Friestad G. K.; Mathies A. K. Tetrahedron 2007, 63, 2541. doi: 10.1016/j.tet.2006.11.076 pmid: 11749440
	(j) Kizirian J.-C. Chem. Rev. 2008, 108, 140. doi: 10.1021/cr040107v pmid: 11749440
	(k) Chen D.; Xu M.-H. Chin. J. Org. Chem. 2017, 37, 1589. (in Chinese) doi: 10.6023/cjoc201704017 pmid: 11749440
	陈雕, 徐明华, 有机化学, 2017, 37, 1589.). doi: 10.6023/cjoc201704017 pmid: 11749440
	(l) Tang L.; Li X.; Xie F.; Zhang W. Chin. J. Org. Chem. 2020, 40, 575. (in Chinese) doi: 10.6023/cjoc201910010 pmid: 11749440
	唐亮, 李雪薇, 谢芳, 张万斌, 有机化学, 2020, 40, 575.). doi: 10.6023/cjoc201910010 pmid: 11749440
	(m) Sun Z.; Zhang C.; Chen L.; Xie H.; Liu B.; Liu D. Chin. J. Org. Chem. 2021, 41, 1789. (in Chinese) pmid: 11749440
	孙忠文, 张聪聪, 陈丽君, 谢惠定, 柳波, 刘丹丹, 有机化学, 2021, 41, 1789.). doi: 10.6023/cjoc202011005 pmid: 11749440
	(n) Liu B.; Xu M.-H. Chin. Sci. Bull. 2021, 66, 3251. (in Chinese) doi: 10.1360/TB-2021-0008 pmid: 11749440
	( 刘博, 徐明华, 科学通报, 2021, 66, 3251.) pmid: 11749440
[2]	(a) Mgller T. E.; Hultzsch K. C.; Yus M.; Foubelo F.; Tada M. Chem. Rev. 2008, 108, 3795. doi: 10.1021/cr0306788 pmid: 20677749
	(b) Nugent T. C.; El-Shazly M. Adv. Synth. Catal. 2010, 352, 753. doi: 10.1002/adsc.200900719 pmid: 20677749
	(c) Candeias N. R.; Montalbano F.; Cal P. M. S. D.; Gois P. M. P. Chem. Rev. 2010, 110, 6169. doi: 10.1021/cr100108k pmid: 20677749
	(d) Wang C.; Villa-Marcos B.; Xiao J. Chem. Commun. 2011, 47, 9773. doi: 10.1039/c1cc12326b pmid: 20677749
	(e) Xie J.-H.; Zhu S.-F., Zhou Q.-L. Chem. Soc. Rev. 2012, 41, 4126. doi: 10.1039/c2cs35007f pmid: 20677749
	(f) Huang Y.-Y.; Cai C.; Yang X.; Lv Z.-C.; Schneider U. ACS Catal. 2016, 6, 5747. doi: 10.1021/acscatal.6b01725 pmid: 20677749
	(g) Wu P.; Givskov M.; Nielsen T. E. Chem. Rev. 2019, 119, 11245. doi: 10.1021/acs.chemrev.9b00214 pmid: 20677749
[3]	Petasis N. A.; Akritopoulou I. Tetrahedron Lett. 1993, 34, 583. doi: 10.1016/S0040-4039(00)61625-8
[4]	Hall D. Boronic Acid: Preparation and Applications in Organic Synthesis and Medicine, Wiley-VCH, Weinheim, Germany, 2005, pp. 279-304.
[5]	Yang X.; Cao Z.-H.; Zhou Y.; Cheng F.; Lin Z.-W.; Ou Z.; Yuan Y.; Huang Y.-Y. Org. Lett. 2018, 20, 2585. doi: 10.1021/acs.orglett.8b00721
[6]	(a) Zhu J.; Bienaymé H. Multicomponent Reactions, Wiley-VCH, Weineim, Germany, 2005, pp. 206-223.
	(b) Kürti L.; Czakó B. Strategic Applications of Named Reactions in Organic Synthesis, Eds.: Hayhurst, J., Elsevier, London, 2005, p. 340.
	(c) Yu T.; Li H.; Wu X.; Yang J. Chin. J. Org. Chem. 2012, 32, 1836. (in Chinese) doi: 10.6023/cjoc1202092
	( 于涛, 李慧, 伍新燕, 杨军, 有机化学, 2012, 32, 1836.) doi: 10.6023/cjoc1202092
[7]	Petasis N. A.; Zavialov I. A. J. Am. Chem. Soc. 1997, 119, 445. doi: 10.1021/ja963178n
[8]	Petasis N. A.; Goodman A.; Zavialov I. A. Tetrahedron 1997, 53, 16463. doi: 10.1016/S0040-4020(97)01028-4
[9]	Southwood T. J.; Curry M. C.; Hutton C. A. Tetrahedron 2006, 62, 236. doi: 10.1016/j.tet.2005.09.114
[10]	Churches Q. I.; Stewart H. E.; Cohen S. B.; Shröder A.; Turner P.; Hutton C. A. Pure. Appl. Chem. 2008, 80, 687. doi: 10.1351/pac200880040687
[11]	Churches Q. I.; Johnson J. K.; Fifer N. L.; Hutton C. A. Aust. J. Chem. 2011, 64, 62. doi: 10.1071/CH10341
[12]	Jiang B.; Yang C.-G.; Gu X.-H. Tetrahedron Lett. 2001, 42, 2545. doi: 10.1016/S0040-4039(01)00229-5
[13]	Jiang B.; Xu M. Org. Lett. 2002, 4, 4077. pmid: 12423090
[14]	Shevchuk M. V.; Sorochinsky A. E.; Khilya V. P.; Romanenko V. D.; Kukhar V. P. Synlett 2010, 73.
[15]	Morozova V. A.; Beletskaya I. P.; Titanyuk I. D. Tetrahedron: Asymmetry 2017, 28, 349. doi: 10.1016/j.tetasy.2017.01.001
[16]	Tan Q.-Y.; Wang X.-Q.; Xiong Y.; Zhao Z.-M.; Lu L.; Tang P.; Zhang M. Angew. Chem., Int. Ed. 2017, 56, 4829. doi: 10.1002/anie.201700581
[17]	Lin Z.-W.; Zhou Y.; Zhao Z.-N.; Zhao Y.; Liu J.; Huang Y.-Y. Org. Chem. Front. 2019, 6, 751. doi: 10.1039/C8QO01428K
[18]	Xie Y.-W.; Zhao Z.-N.; Lin Z.-W.; Wang Y.-H.; Liu Y.-Q.; Huang Y.-Y. Chem. Commun. 2021, 57, 2364. doi: 10.1039/D0CC08241D
[19]	Petasis N. A.; Patel Z. D. Tetrahedron Lett. 2000, 41, 9607. doi: 10.1016/S0040-4039(00)01717-2
[20]	Churches Q. I.; White J. M.; Hutton C. A. Org. Lett. 2011, 13, 2900. doi: 10.1021/ol200917s pmid: 21561144
[21]	Li Y.; Xu M.-H. Org. Lett. 2012, 14, 2062. doi: 10.1021/ol300581n
[22]	For related crystal structures and theoretical calculations: (a) Owens T. D.; Hollander F. J.; Oliver A. G.; Ellman J. A. J. Am. Chem. Soc. 2001, 123, 1539. doi: 10.1021/ja005635c pmid: 12583765
	(b) Owens T. D.; Souers A. J.; Ellman J. A. J. Org. Chem. 2003, 68, 3. doi: 10.1021/jo020524c pmid: 12583765
	(c) Schenkel L. B.; Ellman J. A. Org. Lett. 2003, 5, 545. pmid: 12583765
	(d) Tietze L. F.; Schuffenhauer A. Eur. J. Org. Chem. 1998, 1629. pmid: 12583765
	(e) Bharatam P. V.; Uppal P.; Kaur A.; Kaur D. J. Chem. Soc. Perkin Trans. 2, 2000, 43. pmid: 12583765
[23]	Bursavich M. G.; Harrison B. A.; Acharya R.; Costa D. E.; Freeman E. A.; Hodgdon H. E.; Hrdlicka L. A.; Jin H.; Kapadnis S.; Moffit J. S.; Murphy D. A.; Nolan S.; Patzke H.; Tang C.; Wen M.; Koenig G.; Blain J.-F.; BurnettOrcid D. A. J. Med. Chem. 2017, 60, 2383. doi: 10.1021/acs.jmedchem.6b01620 pmid: 28230986
[24]	Wang J.; Xu B.; Si S.; Li H.; Song G. Mol. Divers. 2014, 18, 887. doi: 10.1007/s11030-014-9531-9
[25]	Lenci E.; Rossi A.; Menchi G.; Trabocchi A. Org. Biomol. Chem. 2017, 15, 9710. doi: 10.1039/C7OB02454A
[26]	Kumagai N.; Muncipinto G.; Schreiber S.L. Angew. Chem., Int. Ed. 2006, 45, 3635. doi: 10.1002/(ISSN)1521-3773
[27]	Ascic E.; Quement S. T. L.; Ishoey M.; Daugaard M.; Nielsen T. E. ACS Comb. Sci. 2012, 14, 253. doi: 10.1021/co300001e
[28]	Wu P.; Petersen M. Å.; Cohrt A. E.; Petersen R.; Clausen M. H.; Nielsen T. E. Eur. J. Org. Chem. 2015, 2346.
[29]	(a) Flagstad T.; Hansen M. R.; Le Quement S. T.; Givskov M.; Nielsen T. E. ACS Comb. Sci. 2015, 17, 19. doi: 10.1021/co500091f pmid: 25469710
	(b) Le Quement S. T.; Flagstad T.; Mikkelsen R. J. T.; Hansen M. R.; Givskov M. C.; Nielsen T. E. Org. Lett. 2012, 14, 640. doi: 10.1021/ol203280b pmid: 25469710
[30]	Jarvis S. B. D.; Charette A. B. Org. Lett. 2011, 13, 3830. doi: 10.1021/ol201349k pmid: 21707119
[31]	Mandai H.; Yamada H.; Shimowaki K.; Mitsudo K.; Suga S. Synthesis 2014, 46, 2672 doi: 10.1055/s-00000084
[32]	Cannillo A.; Norsikian S.; Retailleau P.; Dau M.-E. T. H.; Iorga B. I.; Beau J.-M. Chem. Eur. J. 2013, 19, 9127. doi: 10.1002/chem.201301712
[33]	Thaima T.; Pyne S. G. Org. Lett. 2015, 17, 778. doi: 10.1021/ol503424k
[34]	Liepouri F.; Bernasconi G.; Petasis N. A. Org. Lett. 2015, 17, 1628. doi: 10.1021/acs.orglett.5b00024 pmid: 25790269
[35]	Flagstad T.; Petersen M. T.; Nielsen T. E. Angew. Chem., Int. Ed. 2015, 54, 8395. doi: 10.1002/anie.201502989
[36]	Norsikian S.; Beretta M.; Cannillo A.; Martin A.; Retailleau P.; Beau J.-M. Chem. Commun. 2015, 51, 9991. doi: 10.1039/C5CC01716E
[37]	Norsikian S.; Beretta M.; Cannillo A.; Auvray M.; Martin A.; Retailleau P.; Iorga B. I.; Beau J.-M. Eur. J. Org. Chem. 2017, 1940.
[38]	Liew S. K.; He Z.; St. Denis, J. D.; Yudin, A. K. J. Org. Chem. 2013, 78, 11637. doi: 10.1021/jo401489q
[39]	Chevis P. J.; Wangngae S.; Thaima T.; Carroll A. W.; Willis A. C.; Pattarawarapan M.; Pyne S. G. Chem. Commun. 2019, 55, 6050. doi: 10.1039/C9CC02765C
[40]	Koolmeister T.; Södergren M.; Scobie M. Tetrahedron Lett. 2002, 43, 5969. doi: 10.1016/S0040-4039(02)01263-7
[41]	Hellou N.; Macé A.; Martin C.; Dorcet V.; Roisnel T.; Jean M.; Vanthuyne N.; Berrée F.; Carboni B.; Crassous J. J. Org. Chem. 2018, 83, 484. doi: 10.1021/acs.joc.7b02619 pmid: 29224347
[42]	Yamaoka Y.; Miyabe H.; Takemoto Y. J. Am. Chem. Soc. 2007, 129, 6686. doi: 10.1021/ja071470x
[43]	Inokuma T.; Suzuki Y.; Sakaeda T.; Takemoto Y. Chem. Asian J. 2011, 6, 2902. doi: 10.1002/asia.v6.11
[44]	Lou S.; Schaus S. E. J. Am. Chem. Soc. 2008, 130, 6922. doi: 10.1021/ja8018934
[45]	Muncipinto G.; Moquist P. N.; Schreiber S. L.; Schaus S. E. Angew. Chem., Int. Ed. 2011, 50, 8172. doi: 10.1002/anie.v50.35
[46]	Jiang Y.; Schaus S. E. Angew. Chem., Int. Ed. 2017, 56, 1544. doi: 10.1002/anie.v56.6
[47]	Han W.-Y.; Wu Z.-J.; Zhang X.-M.; Yuan W.-C. Org. Lett. 2012, 14, 976. doi: 10.1021/ol203109a
[48]	Han W.-Y.; Zuo J.; Zhang X.-M.; Yuan W.-C. Tetrahedron 2013, 69, 537. doi: 10.1016/j.tet.2012.11.043
[49]	Shi X.; Kiesman W. F.; Levina A.; Xin Z. J. Org. Chem. 2013, 78, 9415. doi: 10.1021/jo4016425
[50]	(a) Au C. W. G.; Nash R. J.; Pyne S. G. Chem. Commun. 2010, 46, 713. doi: 10.1039/B918233K pmid: 25668389
	(b) Ghosal P.; Shaw A. K. J. Org. Chem. 2012, 77, 7627. doi: 10.1021/jo300804d pmid: 25668389
	(c) Bouillon M. E.; Pyne S. G. Tetrahedron Lett. 2014, 55, 475. pmid: 25668389
	(d) Carroll A. W.; Savaspun K.; Willis A. C.; Hoshino M.; Kato A.; Pyne S. G. J. Org. Chem. 2018, 83, 5558. doi: 10.1021/acs.joc.8b00585 pmid: 25668389
	(e) Ritthiwigrom T.; Au C. W. G.; Pyne S. G. Curr. Org. Synth. 2012, 9, 583. doi: 10.2174/157017912803251765 pmid: 25668389
	(f) Miller K. E.; Wright A. J.; Olesen M. K.; Hovey M. T.; Scheerer J. R. J. Org. Chem. 2015, 80, 1569. doi: 10.1021/jo502493e pmid: 25668389
	(g) Matthies S.; Stallforth P.; Seeberger P. H. J. Am. Chem. Soc. 2015, 137, 2848. doi: 10.1021/jacs.5b00455 pmid: 25668389
	(h) Hassan M. I.; Lundgren B. R.; Chaumun M.; Whitfield D. M.; Clark B.; Schoenhofen I. C.; Boddy C. N. Angew. Chem., Int. Ed. 2016, 55, 12018. doi: 10.1002/anie.201606006 pmid: 25668389
[51]	Sim Y. E.; Nwajiobi O.; Mahesh S.; Cohen R. D.; Reibarkh M. Y.; Raj M. Chem. Sci. 2020, 11, 53. doi: 10.1039/C9SC04697F

不对称Petasis反应在手性胺类化合物合成中的应用

Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 51

References 51

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Zhanglong Yu, Zhongliang Li, Changjiang Yang, Qiangshuai Gu, Xinyuan Liu. Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★ [J]. Acta Chimica Sinica, 2023, 81(8): 955-966.
[2]	Shuang Yang, Ningyi Wang, Qingqing Hang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★ [J]. Acta Chimica Sinica, 2023, 81(7): 793-808.
[3]	Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li. Gold/Iridium Catalyzed Alkynylamide Cyclization/Asymmetric Allylic Benzylation Cascade Reaction^★ [J]. Acta Chimica Sinica, 2023, 81(5): 431-434.
[4]	Xueyang Yin, Kai Gu, Zhengzhong Shao. Preparation of the Protein/Polyphenylboronic Acid Nanospheres for Drug Loading and Unloading [J]. Acta Chimica Sinica, 2023, 81(2): 116-123.
[5]	Yang Gao, Xuexin Zhang, Jinsheng Yu, Jian Zhou. Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1590-1608.
[6]	Qingduan Meng, Jiahong Han, Yixiao Pan, Wei Hao, Qing-Hua Fan. Asymmetric Synthesis of C₁-Symmetric Chiral N-Heterocyclic Carbene (NHC) Ligands and Their Applications in Asymmetric Catalysis^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1271-1279.
[7]	Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes [J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164.
[8]	Jinyue Ma, Lufei Huang, Baowen Zhou, Lin Yao. Construction and Catalysis Advances of Inorganic Chiral Nanostructures [J]. Acta Chimica Sinica, 2022, 80(11): 1507-1523.
[9]	Qing-Ru Zhao, Ru Jiang, Shu-Li You. Ir-catalyzed Sequential Asymmetric Allylic Substitution/Olefin Isomerization for the Synthesis of Axially Chiral Compounds [J]. Acta Chimica Sinica, 2021, 79(9): 1107-1112.
[10]	Bo-Shuai Mu, Zhi-Hao Zhang, Wen-Biao Wu, Jin-Sheng Yu, Jian Zhou. Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines [J]. Acta Chimica Sinica, 2021, 79(6): 685-693.
[11]	Zhuoji Deng, Yifan Ouyang, Yunlin Ao, Qian Cai. Copper(I)-Catalyzed Asymmetric Desymmetric Intramolecular Alkenyl C—N Coupling Reaction [J]. Acta Chimica Sinica, 2021, 79(5): 649-652.
[12]	Yang Shang, Jian Xiao, Yawen Wang, Yu Peng. Advances on Asymmetric Construction of Diarylmethine Stereocenters [J]. Acta Chimica Sinica, 2021, 79(11): 1303-1319.
[13]	Zhu Ren-Yi, Liao Kui, Yu Jin-Sheng, Zhou Jian. Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Acta Chimica Sinica, 2020, 78(3): 193-216.
[14]	Cheng Lei, Zhou Qilin. Advances on Nickel-Catalyzed C(sp³)-C(sp³) Bond Formation [J]. Acta Chimica Sinica, 2020, 78(10): 1017-1029.
[15]	Wang Qiang, Gu Qing, You Shu-Li. Recent Progress on Transition-Metal-Catalyzed Asymmetric C-H Bond Functionalization for the Synthesis of Biaryl Atropisomers [J]. Acta Chim. Sinica, 2019, 77(8): 690-704.