Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation

doi:10.6023/cjoc202005037

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2904-2911.DOI: 10.6023/cjoc202005037 Previous Articles Next Articles

基于化学和对映选择性转移氢化的β,γ-炔基α-氨基酸酯的催化不对称合成研究

张璐^a, 刘爱芹^c, 刘华铮^a, 万仁忠^a, 孙书涛^b, 刘磊^b

a 山东农业大学动物科技学院山东泰安 271018;
b 山东大学化学与化工学院济南 250100;
c 山东第一医科大学(山东省医学科学院)药物研究所济南 250062

收稿日期:2020-05-15 修回日期:2020-06-03 发布日期:2020-06-13
通讯作者: 万仁忠, 孙书涛, 刘磊 E-mail:wrzh63@163.com;sunshutao@sdu.edu.cn;leiliu@sdu.edu.cn
基金资助:
国家自然科学基金（Nos.21722204，21971148）资助项目.

Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation

Zhang Lu^a, Liu Aiqin^c, Liu Huazheng^a, Wan Renzhong^a, Sun Shutao^b, Liu Lei^b

a College of Animal Science and Veterinary Medicine, Shandong Agricultural University, Taian, Shandong 271018;
b School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100;
c Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250062

Received:2020-05-15 Revised:2020-06-03 Published:2020-06-13
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21722204, 21971148).

1. cjoc202005037.pdf(1920KB)

Abstract

An effective chemo- and enantioselective transfer hydrogenation of β,γ-alkynyl α-imino esters to prepare optically pure β,γ-alkynyl α-amino esters has been described. The excellent chemoselectivity was achieved by using chiral phosphoric acid catalyzed asymmetric reduction with benzothiazoline as hydride donor. The reaction exhibited good functional group tolerance, providing a range of optically active non-natural amino esters with excellent enantioselectivity.

Key words: β,γ-alkynyl α-amino ester, chemoselectivity, enantioselectivity, transfer hydrogenation, benzothiazoline

Cite this article

Zhang Lu, Liu Aiqin, Liu Huazheng, Wan Renzhong, Sun Shutao, Liu Lei. Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2904-2911.

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[1] (a) Afagh, N. A.; Yudin, A. K. Angew. Chem., Int. Ed. 2010, 49, 262.
(b) Mahatthananchai, J.; Dumas, A.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 10954.
(c) Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc. Rev. 2013, 42, 9155.
[2] (a) Hoffmann, R. W. Synthesis 2006, 3531.
(b) Young, I. S.; Baran, P. S. Nat. Chem. 2009, 1, 193.
[3] Trost, B. M. Science 1991, 254, 1471.
[4] Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40.
[5] (a) Barrett, G. C. Chemistry and Biochemistry of the Amino Acids, Chapman & Hall, London, 1985.
(b) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989.
(c) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
(d) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
(e) Chin, J. W.; Cropp, T. A.; Anderson, J. C.; Mukherji, M.; Zhang, Z.; Schultz, P. G. Science 2002, 301, 964.
(f) Wang, L.; Schultz, P. G. Angew. Chem., Int. Ed. 2004, 44, 34.
(g) Cropp, T. A.; Schultz, P. G. Trends Genet. 2004, 20, 625.
[6] (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
(b) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
(c) Lygo, B.; Angrews, B. I. Acc. Chem. Res. 2004, 37, 518.
(d) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626.
[7] (a) Abdulganeeva, S. A.; Erzhanov, K. B. Russ. Chem. Rev. 1991, 60, 676.
(b) Williams, R. M.; Aldous, D. J.; Aldous, S. C. J. Org. Chem. 1990, 55, 4657.
(c) Castelhano, A. L.; Horne, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451.
[8] (a) Ji, J.-X.; Wu, J.; Chan, A. S. C. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 11196.
(b) Rueping, M.; Antonchick, A. P.; Brinkmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903.
[9] (a) Kang, Q.; Zhao, Z.-A.; You, S.-L. Org. Lett. 2008, 10, 2031.
(b) Chen, M.-W.; Wu, B.; Chen, Z.-P.; Shi, L.; Zhou, Y.-G. Org. Lett. 2016, 18, 4650.
[10] (a) Ge, X.; Chen, X.; Qian, C. Chin. J. Org. Chem. 2016, 36, 1208(in Chinese). (葛新, 陈新志, 钱超, 有机化学, 2016, 36, 1208.)
(b) Hu, S.-B.; Chen, M.-W.; Zhai, X.-Y.; Zhou, Y.-G. Acta Chim. Sinica 2018, 76, 103(in Chinese). (胡书博, 陈木旺, 翟小勇, 周永贵, 化学学报, 2018, 76, 103.)
(c) Liu, Y.; Dong, X.-Q.; Zhang, X. Chin. J. Org. Chem. 2020, 40, 1096(in Chinese). (刘元华, 董秀琴, 张绪穆, 有机化学, 2020, 40, 1096.)
(d) Dou, X.; Liu, D.; Zhang, W. Chin. J. Pharm. 2020, 51, 551(in Chinese). (窦骁勇, 刘德龙, 张万斌, 中国医药工业杂志, 2020, 51, 551.)
[11] Zhang, L.; Zhu, R.; Feng, A.; Zhao, C.; Chen, L.; Feng, G.; Liu, L. Chem. Sci. 2020, 11, 4444.
[12] (a) Zhu, C.; Saito, K.; Yamanaka, M.; Akiyama, T. Acc. Chem. Res. 2015, 48, 388.
(b) Zhu, C.; Falck, J. R. ChemCatChem 2011, 3, 1850.
(c) Zhu, C.; Akiyama, T. Org. Lett. 2009, 11, 4180.
(d) Henseler, A.; Kato, M.; Mori, K.; Akiyama, T. Angew. Chem., Int. Ed. 2011, 50, 8180.
(e) Horiguchi, K.; Yamamoto, E.; Saito, K.; Yamanaka, M.; Akiyama, T. Chem.-Eur. J. 2016, 22, 8078.
(f) Kim, K.-H.; Akiyama, T.; Cheon, C.-H. Chem.-Asian J. 2016, 11, 274.
(g) Wen, W.; Zeng, Y.; Peng, L.-Y.; Fu, L.-N.; Guo, Q.-X. Org. Lett. 2015, 17, 3922.
[13] Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2011, 50, 8180.
[14] Chen, X. M.; Li, X. S.; Chan, A. S. C. Chin. Chem. Lett. 2009, 20, 407.
[15] Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42.

基于化学和对映选择性转移氢化的β,γ-炔基α-氨基酸酯的催化不对称合成研究

Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation

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