Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines
Received date: 2021-08-21
Online published: 2021-09-24
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.
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 . DOI: 10.6023/A21080391
| [1] | (a) Kobayashi S.; Ishitani H. Chem. Rev. 1999, 99, 1069. |
| [1] | (b) Ellman J. A.; Owens T. D.; Tang T. P. Acc. Chem. Res. 2002, 35, 984. |
| [1] | (c) Blaser H.-U.; Malan C.; Pugin B.; Spindler F.; Steiner H.; Studer M. Adv. Synth. Catal. 2003, 345, 103. |
| [1] | (d) Ellman J. A. Pure Appl. Chem. 2003, 75, 39. |
| [1] | (e) Kukula P.; Prins R. Top. Catal. 2003, 25, 29. |
| [1] | (f) Morton D.; Stockman R. A. Tetrahedron 2006, 62, 8869. |
| [1] | (g) Ramachandran P. V.; Burghardt T. E. Pure Appl. Chem. 2006, 78, 1397. |
| [1] | (h) Skucas E.; Ngai M.-Y.; Komanduri V.; Krische M. J. Acc. Chem. Res. 2007, 40, 1394. |
| [1] | (i) Friestad G. K.; Mathies A. K. Tetrahedron 2007, 63, 2541. |
| [1] | (j) Kizirian J.-C. Chem. Rev. 2008, 108, 140. |
| [1] | (k) Chen D.; Xu M.-H. Chin. J. Org. Chem. 2017, 37, 1589. (in Chinese) |
| [1] | 陈雕, 徐明华, 有机化学, 2017, 37, 1589.). |
| [1] | (l) Tang L.; Li X.; Xie F.; Zhang W. Chin. J. Org. Chem. 2020, 40, 575. (in Chinese) |
| [1] | 唐亮, 李雪薇, 谢芳, 张万斌, 有机化学, 2020, 40, 575.). |
| [1] | (m) Sun Z.; Zhang C.; Chen L.; Xie H.; Liu B.; Liu D. Chin. J. Org. Chem. 2021, 41, 1789. (in Chinese) |
| [1] | 孙忠文, 张聪聪, 陈丽君, 谢惠定, 柳波, 刘丹丹, 有机化学, 2021, 41, 1789.). |
| [1] | (n) Liu B.; Xu M.-H. Chin. Sci. Bull. 2021, 66, 3251. (in Chinese) |
| [1] | ( 刘博, 徐明华, 科学通报, 2021, 66, 3251.) |
| [2] | (a) Mgller T. E.; Hultzsch K. C.; Yus M.; Foubelo F.; Tada M. Chem. Rev. 2008, 108, 3795. |
| [2] | (b) Nugent T. C.; El-Shazly M. Adv. Synth. Catal. 2010, 352, 753. |
| [2] | (c) Candeias N. R.; Montalbano F.; Cal P. M. S. D.; Gois P. M. P. Chem. Rev. 2010, 110, 6169. |
| [2] | (d) Wang C.; Villa-Marcos B.; Xiao J. Chem. Commun. 2011, 47, 9773. |
| [2] | (e) Xie J.-H.; Zhu S.-F., Zhou Q.-L. Chem. Soc. Rev. 2012, 41, 4126. |
| [2] | (f) Huang Y.-Y.; Cai C.; Yang X.; Lv Z.-C.; Schneider U. ACS Catal. 2016, 6, 5747. |
| [2] | (g) Wu P.; Givskov M.; Nielsen T. E. Chem. Rev. 2019, 119, 11245. |
| [3] | Petasis N. A.; Akritopoulou I. Tetrahedron Lett. 1993, 34, 583. |
| [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. |
| [6] | (a) Zhu J.; Bienaymé H. Multicomponent Reactions, Wiley-VCH, Weineim, Germany, 2005, pp. 206-223. |
| [6] | (b) Kürti L.; Czakó B. Strategic Applications of Named Reactions in Organic Synthesis, Eds.: Hayhurst, J., Elsevier, London, 2005, p. 340. |
| [6] | (c) Yu T.; Li H.; Wu X.; Yang J. Chin. J. Org. Chem. 2012, 32, 1836. (in Chinese) |
| [6] | ( 于涛, 李慧, 伍新燕, 杨军, 有机化学, 2012, 32, 1836.) |
| [7] | Petasis N. A.; Zavialov I. A. J. Am. Chem. Soc. 1997, 119, 445. |
| [8] | Petasis N. A.; Goodman A.; Zavialov I. A. Tetrahedron 1997, 53, 16463. |
| [9] | Southwood T. J.; Curry M. C.; Hutton C. A. Tetrahedron 2006, 62, 236. |
| [10] | Churches Q. I.; Stewart H. E.; Cohen S. B.; Shröder A.; Turner P.; Hutton C. A. Pure. Appl. Chem. 2008, 80, 687. |
| [11] | Churches Q. I.; Johnson J. K.; Fifer N. L.; Hutton C. A. Aust. J. Chem. 2011, 64, 62. |
| [12] | Jiang B.; Yang C.-G.; Gu X.-H. Tetrahedron Lett. 2001, 42, 2545. |
| [13] | Jiang B.; Xu M. Org. Lett. 2002, 4, 4077. |
| [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. |
| [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. |
| [17] | Lin Z.-W.; Zhou Y.; Zhao Z.-N.; Zhao Y.; Liu J.; Huang Y.-Y. Org. Chem. Front. 2019, 6, 751. |
| [18] | Xie Y.-W.; Zhao Z.-N.; Lin Z.-W.; Wang Y.-H.; Liu Y.-Q.; Huang Y.-Y. Chem. Commun. 2021, 57, 2364. |
| [19] | Petasis N. A.; Patel Z. D. Tetrahedron Lett. 2000, 41, 9607. |
| [20] | Churches Q. I.; White J. M.; Hutton C. A. Org. Lett. 2011, 13, 2900. |
| [21] | Li Y.; Xu M.-H. Org. Lett. 2012, 14, 2062. |
| [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. |
| [22] | (b) Owens T. D.; Souers A. J.; Ellman J. A. J. Org. Chem. 2003, 68, 3. |
| [22] | (c) Schenkel L. B.; Ellman J. A. Org. Lett. 2003, 5, 545. |
| [22] | (d) Tietze L. F.; Schuffenhauer A. Eur. J. Org. Chem. 1998, 1629. |
| [22] | (e) Bharatam P. V.; Uppal P.; Kaur A.; Kaur D. J. Chem. Soc. Perkin Trans. 2, 2000, 43. |
| [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. |
| [24] | Wang J.; Xu B.; Si S.; Li H.; Song G. Mol. Divers. 2014, 18, 887. |
| [25] | Lenci E.; Rossi A.; Menchi G.; Trabocchi A. Org. Biomol. Chem. 2017, 15, 9710. |
| [26] | Kumagai N.; Muncipinto G.; Schreiber S.L. Angew. Chem., Int. Ed. 2006, 45, 3635. |
| [27] | Ascic E.; Quement S. T. L.; Ishoey M.; Daugaard M.; Nielsen T. E. ACS Comb. Sci. 2012, 14, 253. |
| [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. |
| [29] | (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. |
| [30] | Jarvis S. B. D.; Charette A. B. Org. Lett. 2011, 13, 3830. |
| [31] | Mandai H.; Yamada H.; Shimowaki K.; Mitsudo K.; Suga S. Synthesis 2014, 46, 2672 |
| [32] | Cannillo A.; Norsikian S.; Retailleau P.; Dau M.-E. T. H.; Iorga B. I.; Beau J.-M. Chem. Eur. J. 2013, 19, 9127. |
| [33] | Thaima T.; Pyne S. G. Org. Lett. 2015, 17, 778. |
| [34] | Liepouri F.; Bernasconi G.; Petasis N. A. Org. Lett. 2015, 17, 1628. |
| [35] | Flagstad T.; Petersen M. T.; Nielsen T. E. Angew. Chem., Int. Ed. 2015, 54, 8395. |
| [36] | Norsikian S.; Beretta M.; Cannillo A.; Martin A.; Retailleau P.; Beau J.-M. Chem. Commun. 2015, 51, 9991. |
| [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. |
| [39] | Chevis P. J.; Wangngae S.; Thaima T.; Carroll A. W.; Willis A. C.; Pattarawarapan M.; Pyne S. G. Chem. Commun. 2019, 55, 6050. |
| [40] | Koolmeister T.; Södergren M.; Scobie M. Tetrahedron Lett. 2002, 43, 5969. |
| [41] | Hellou N.; Mace? A.; Martin C.; Dorcet V.; Roisnel T.; Jean M.; Vanthuyne N.; Berre?e F.; Carboni B.; Crassous J. J. Org. Chem. 2018, 83, 484. |
| [42] | Yamaoka Y.; Miyabe H.; Takemoto Y. J. Am. Chem. Soc. 2007, 129, 6686. |
| [43] | Inokuma T.; Suzuki Y.; Sakaeda T.; Takemoto Y. Chem. Asian J. 2011, 6, 2902. |
| [44] | Lou S.; Schaus S. E. J. Am. Chem. Soc. 2008, 130, 6922. |
| [45] | Muncipinto G.; Moquist P. N.; Schreiber S. L.; Schaus S. E. Angew. Chem., Int. Ed. 2011, 50, 8172. |
| [46] | Jiang Y.; Schaus S. E. Angew. Chem., Int. Ed. 2017, 56, 1544. |
| [47] | Han W.-Y.; Wu Z.-J.; Zhang X.-M.; Yuan W.-C. Org. Lett. 2012, 14, 976. |
| [48] | Han W.-Y.; Zuo J.; Zhang X.-M.; Yuan W.-C. Tetrahedron 2013, 69, 537. |
| [49] | Shi X.; Kiesman W. F.; Levina A.; Xin Z. J. Org. Chem. 2013, 78, 9415. |
| [50] | (a) Au C. W. G.; Nash R. J.; Pyne S. G. Chem. Commun. 2010, 46, 713. |
| [50] | (b) Ghosal P.; Shaw A. K. J. Org. Chem. 2012, 77, 7627. |
| [50] | (c) Bouillon M. E.; Pyne S. G. Tetrahedron Lett. 2014, 55, 475. |
| [50] | (d) Carroll A. W.; Savaspun K.; Willis A. C.; Hoshino M.; Kato A.; Pyne S. G. J. Org. Chem. 2018, 83, 5558. |
| [50] | (e) Ritthiwigrom T.; Au C. W. G.; Pyne S. G. Curr. Org. Synth. 2012, 9, 583. |
| [50] | (f) Miller K. E.; Wright A. J.; Olesen M. K.; Hovey M. T.; Scheerer J. R. J. Org. Chem. 2015, 80, 1569. |
| [50] | (g) Matthies S.; Stallforth P.; Seeberger P. H. J. Am. Chem. Soc. 2015, 137, 2848. |
| [50] | (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. |
| [51] | Sim Y. E.; Nwajiobi O.; Mahesh S.; Cohen R. D.; Reibarkh M. Y.; Raj M. Chem. Sci. 2020, 11, 53. |
/
| 〈 |
|
〉 |
