Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes

doi:10.6023/cjoc201602018

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1805-1813.DOI: 10.6023/cjoc201602018 Previous Articles Next Articles

REVIEW

磷亲核试剂对缺电子烯烃不对称共轭加成反应的进展

李振^a, 段伟良^b

a 上海应用技术学院化学与环境工程学院上海 201418;
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2016-02-19 修回日期:2016-04-20 发布日期:2016-04-29
通讯作者: 段伟良 E-mail:wlduan@mail.sioc.ac.cn
基金资助:
国家自然科学基金（Nos. 20902099，21172238，21472218）资助项目.

Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes

Li Zhen^a, Duan Weiliang^b

a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2016-02-19 Revised:2016-04-20 Published:2016-04-29
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20902099, 21172238, 21472218).

Chiral phosphines are very useful in the fields of asymmetric catalysis, pharmaceutical chemistry, and materials. These compounds have been used as ligands coordinated to transition metals or organocatalysts in various reactions to furnish optically active products with high efficiency. Asymmetric phosphorus-addition reaction can be utilized for the direct preparation of chiral phosphorus compounds. This review summarizes the recent progress in the field of enantioselective phosphorus-addition reactions. Several examples of transition metal- and organocatalyst-promoted asymmetric hydrophosphination reactions of electron-deficient alkenes have been introduced.

Key words: asymmetric addition, phosphorus nucleophiles, chiral phosphorus compounds, electron-deficient alkenes

Cite this article

Li Zhen, Duan Weiliang. Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes[J]. Chin. J. Org. Chem., 2016, 36(8): 1805-1813.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For reviews on metal-catalyzed asymmetric 1,4-addition, see:
(a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
(b) Miyaura, N. Synlett 2009, 2039.
(c) Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279.
For reviews on organocatalytic asymmetric 1,4-addition, see:
(d) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
(e) Vicario, J. L.; Badía, D.; Carrillo, L. Synthesis 2007, 2065.
(f) Enders, D.; Wang, C.; Liebich, J. X. Chem.-Eur. J. 2009, 15, 11058.
(g) Enders, D.; Lüttgen, K.; Narine, A. A. Synthesis 2007, 959.
(h) Nising, C. F.; Bräse, S. Chem. Soc. Rev. 2008, 37, 1218.
(i) Liu, Q.; Tian, P.; Tong, X.; Lin, G.-Q. Chin. J. Org. Chem. 2015, 35, 1 (in Chinese).
(刘强, 田平, 童晓峰, 林国强, 有机化学, 2015, 35, 1.)
(j) For a review of 1,4-addition reaction of phosphorus nucleophiles to electron-deficient olefins, see: Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 29.
[2] (a) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950.
(b) Scriban, C.; Kovacik, I.; Glueck, D. S. Organometallics 2005, 24, 4871.
[3] For reviews on catalytic asymmetric synthesis of chiral phosphanes, see: (a) Glueck, D. S. Synlett 2007, 2627.
(b) Glueck, D. S. Chem.-Eur. J. 2008, 14, 7108.
(c) Harvey, J. S. Gouverneur, V. Chem. Commun. 2010, 7477.
(d) Zhao, D.; Wang, R. Chem. Soc. Rev. 2012, 41, 2095.
(e) Yao, Q.; Wang, A.; Pu, J.; Tang, Y. Chin. J. Org. Chem. 2014, 34, 292 (in Chinese).
(姚秋丽, 王安俊, 蒲家志, 唐瑜敏, 有机化学, 2014, 34, 292.)
[4] (a) Bansal, R. K. Phosphorus Heterocycles II (Topics in Heterocyclic Chemistry, Vol. 21), Springer, Berlin, 2010.
(b) Börner, A. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications, Wiley-VCH, Weinheim, 2008, Vols. 1～3.
(c) Peruzzini, M.; Gonsalvi, L. Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences, Springer, Berlin, 2011.
(d) Xu, Q.; Zhao, C.; Zhou, Y.; Yin, S.; Han, Li. Chin. J. Org. Chem. 2012, 32, 1761 (in Chinese).
(徐清, 赵长秋, 周永波, 尹双凤, 韩立彪, 有机化学, 2012, 32, 1761.)
[5] (a) Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704.
(b) Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012.
[6] Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mazzanti, A.; Sambri, L.; Melchiorre, P. Chem. Commun. 2007, 722.
[7] (a) Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 4504.
(b) Ibrahem, I.; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Cordova, A. Angew. Chem., Int. Ed. 2007, 46, 4507.
(c) Ibrahem, I.; Hammar, P.; Vesely, J.; Rios, R.; Eriksson, L.; Cordova, A. Adv. Synth. Catal. 2008, 350, 1875.
[8] Feng, J.-J.; Chen, X.-F.; Shi, M.; Duan, W.-L. J. Am. Chem. Soc. 2010, 132, 5562.
[9] For reviews on pincer metal complexes, see: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
(b) Selander, N.; Szabó, K. J. Chem. Rev. 2011, 111, 2048.
(c) Hao, X.; Niu, J.; Zhao, X.; Gong, J.; Song, M. Chin. J. Org. Chem. 2013, 33, 663 (in Chinese).
(郝新奇, 牛俊龙, 赵雪梅, 龚军芳, 宋毛平, 有机化学, 2013, 33, 663.)
For synthesis and application of the chiral PCP-PdCl complex, see: (d) Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1997, 38, 1725.
(e) Longmire, J. M.; Zhang, X.; Shang, M. Organometallics 1998, 17, 4374.
[10] (a) Du, D.; Duan, W.-L. Chem. Commun. 2011, 47, 11101.
(b) Chen, Y.-R.; Duan, W.-L. Org. Lett. 2011, 13, 5824.
(c) Feng, J.-J.; Huang, M.; Lin, Z.-Q.; Duan, W.-L. Adv. Synth. Catal. 2012, 354, 3122.
(d) Du, D.; Lin, Z.-Q.; Lu, J.-Z.; Li, C.; Duan, W.-L. Asian J. Org. Chem. 2013, 2, 392.
(e) Lu, J.; Ye, J.; Duan, W.-L. Org. Lett. 2013, 15, 5016.
(f) Huang, M.; Li, C.; Duan, W.-L.; Xu, S. Chem. Commun. 2012, 48, 11148.
[11] Huang, Y.; Pullarkat, S. A.; Li, L.; Leung, P.-H. Chem. Commun. 2010, 6950.
[12] (a) Huang, Y.; Chew, R. J.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Org. Lett. 2011, 13. 5862.
(b) Huang, Y.; Pullarkat, S. A.; Teong, S.; Chew, R. J.; Li, Y.; Leung, P.-H. Organometallics 2012, 31, 4871.
(c) Chew, R. J.; Huang, Y.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Adv. Synth. Catal. 2013, 355, 1403.
(d) Chew, R. J.; Teo, K. Y.; Huang, Y.; Li, B.-B.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Chem. Commun. 2014, 50, 8768.
(e) Chew, R. J.; Lu, Y.; Jia, Y.-X.; Li, B.-B.; Wong, E. H. Y.; Goh, R.; Li, Y.; Huang, Y.; Pullarkat, S. A.; Leung, P.-H. Chem.-Eur. J. 2014, 20, 14514.
(f) Chew, R. J.; Sepp, K.; Li, B.-B.; Li, Y.; Zhu, P.-C.; Tan, N. S.; Leung, P.-H. Adv. Synth. Catal. 2015, 357, 3297.
[13] (a) Yang, X.-Y.; Tay, W. S.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Organometallics 2015, 34, 5196.
(b) Yang, X.-Y.; Tay, W.; Li, Y.; Pullarkat, S.; Leung, P.-H. Chem. Commun. 2016, 52, 4211.
[14] (a) Yang, M.-J.; Liu, Y.-J.; Gong, J.-F.; Song, M.-P. Organometallics 2011, 30, 3793.
(b) Hao, X.-Q.; Zhao, Y.-W.; Yang, J.-J.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. Organometallics 2014, 33, 1801.
(c) Hao, X. Q.; Huang, J. J.; Wang, T.; Lv, J.; Gong, J. F.; Song, M. P. J. Org. Chem. 2014, 79, 9512.
[15] (a) Ding, B.; Zhang, Z.; Xu, Y.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Org. Lett. 2013, 15, 5476.
(b) Xu, Y.; Yang, Z.; Ding, B.; Liu, D.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Tetrahedron 2015, 71, 6832.
[16] For reviews on asymmetric 1,6-addition reactions, see:
(a) Csákÿ, A. G.; la Herran, G. de.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080.
(b) Biju, A. T. ChemCatChem 2011, 3, 1847.
(c) Silva, E. M. P.; Silva, A. M. S. Synthesis 2012, 44, 3109.
[17] (a) Lu, J.; Ye, J.; Duan, W.-L. Chem. Commun. 2014, 50, 698.
(b) Huang, J.; Zhao, M.-X.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 629.
[18] Huang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P.-H. Inorg. Chem. 2012, 51, 2533.
[19] Li, C.; Li, W.-X.; Xu, S.; Duan, W.-L. Org. Chem. Front. 2014, 1, 541.
[20] Chen, Y.-R.; Feng, J.-J.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 595.
[21] Fu, X.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2007, 5058.
[22] (a) Zhao, D.; Yuan, Y.; Chan, Albert S. C.; Wang, R. Chem.-Eur. J. 2009, 15, 2738.
(b) Zhao, D.; Wang, Y.; Mao, L.; Wang. R. Chem.-Eur. J. 2009, 15, 10983.
(c) Zhao, D.; Mao, L.; Wang, Y.; Yang, D.; Zhang, Q.; Wang, R. Org. Lett. 2010, 12, 1880.
(d) Zhao, D.; Mao, L.; Yang, D.; Wang, R. J. Org. Chem. 2010, 75, 6756.
(e) Zhao, D.; Mao, L.; Wang, L.; Yang, D.; Wang. R. Chem. Commun. 2012, 48, 889.
(f) Zhao, D.; Wang, L.; Yang, D.; Zhang, Y.; Wang. R. Chem.-Eur. J. 2012, 7, 881.
[23] Wen, S.; Li, L.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun. 2010, 4806.
[24] Russo, A.; Lattanzi, A. Eur. J. Org. Chem. 2010, 6736.
[25] Luo, X.; Zhou, Z.; Li, X.; Liang, X.; Ye, J. RSC Adv. 2011, 1, 698.
[26] Hatano, M.; Horibe, T.; Ishihara, K. Angew. Chem., Int. Ed. 2013, 52, 4549.
[27] Geng, Z-C.; Zhang, J.-X.; Li, N.; Chen, J.; Huang, X.-F.; Zhang, S.-Y.; Li, H.-Y.; Tao, J.-C.; Wang, X.-W. Tetrahedron 2014, 70, 417.

磷亲核试剂对缺电子烯烃不对称共轭加成反应的进展

Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[2]	Yunshuai Huang, Xiaohui Jin, Fenglian Zhang, Yifeng Wang. 4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1957-1967.
[3]	Zhu Dong-Xing, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 255-275.
[4]	Sun Guijiu, Xiao Fanhua, Duan Weiliang. Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Quinone Monoketals [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 61-68.
[5]	Cai Han, Ouyang Kunbing, Yang Nianfa. Application of Chiral 1,1'-Bi-2-naphthol Polymers in Asymmetric Epoxidation of (E)-α,β-Unsaturated Aryl Ketones [J]. Chin. J. Org. Chem., 2019, 39(5): 1456-1459.
[6]	Kong Shengnan, Qian Xuefeng, Shu Mouhai, Xiao Wende. Asymmetric Addition Reaction Catalyzed by 1- (2-Hydroxynaphtha-len-1-yl)naphthalen-2-ol Functionalized Porous Organic Polymer [J]. Chin. J. Org. Chem., 2018, 38(10): 2754-2760.
[7]	Chen Diao, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines [J]. Chin. J. Org. Chem., 2017, 37(7): 1589-1612.
[8]	Zhang Xun, Yang Nianfa. Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes [J]. Chin. J. Org. Chem., 2017, 37(4): 1027-1032.
[9]	Liu Dacai, Zhu Weijun, Zhang Anlin, Yang Nianfa, Yang Liwen. Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes [J]. Chin. J. Org. Chem., 2015, 35(8): 1797-1801.
[10]	PAN Sheng-Qiang, ZHANG Cong-Hai, LI Ye, YAN Sheng-Jiao, LIN Jun. Convenient Synthesis of Chiral β-Amino Alcohols and Their Asymmetric Catalytic Reactions [J]. Chin. J. Org. Chem., 2011, 31(02): 193-202.
[11]	Zhang, Huiqing; Yuan, Hao ; Zhou, Zhiming*. Asymmetric Addition of Organolithium Reagents to Ferrocenylimines [J]. Chin. J. Org. Chem., 2009, 29(04): 601-605.
[12]	Hui, Ailing^a; Zhang, Jintang^b; WANG, Zhiyong^*,b. Progress in Asymmetric Alkyl Addition to Aldehydes and Ketones Promoted by Tartaric Acid Derivatives [J]. Chin. J. Org. Chem., 2009, 29(03): 334-340.
[13]	LIU, Wen-Jian; XIAO, Yu-Mei; FU, Bin; LI, Nan ; QIN, Zhao-Hai. Progress in Asymmetrically Catalyzed Addition of Organozinc Reagents to Ketones [J]. Chin. J. Org. Chem., 2008, 28(08): 1348-1357.
[14]	YANG Wang-Gui^a, WU Shuai^a, SHI Min*^,a,b. Progress of Organozinc Reagents in Asymmetric Addition Reactions Catalyzed by Sulfur-Containing Chiral Ligands [J]. Chin. J. Org. Chem., 2007, 27(02): 197-208.
[15]	LIU Wen-Min,WANG Pin-An,ZHANG Sheng-Yong*,JIANG Ru. Synthesis of Chiral β-Aminoalcohol and Its Catalysis in the Asymmetric Addition of Diethylzinc to Aldehyde [J]. Chin. J. Org. Chem., 2006, 26(04): 518-522.