Asymmetric N—H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea

doi:10.6023/cjoc201310053

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 107-111.DOI: 10.6023/cjoc201310053 Previous Articles Next Articles

基于醋酸铑、磺酸和手性亚磺酰胺基脲共催化的α-重氮酯与酰胺不对称N—H插入反应研究

倪懿, 郭鑫, 胡文浩, 刘顺英

华东师范大学上海市分子治疗与新药创制工程技术研究中心上海 200062

收稿日期:2013-10-31 修回日期:2013-11-25 发布日期:2013-11-28
通讯作者: 刘顺英 E-mail:syliu@sist.ecnu.edu.cn, Tel./Fax: 86-21-62221237
基金资助:
国家杰出青年科学基金（No. 21125209）；上海市科委重点基础研究基金（No. 12JC1403800）及上海市闵行区高层次选拔人才计划资助项目.

Asymmetric N—H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea

Ni Yi, Guo Xin, Hu Wenhao, Liu Shunying

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062

Received:2013-10-31 Revised:2013-11-25 Published:2013-11-28
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21125209), the Science and Technology Commission of Shanghai Municipality (No. 12JC1403800) and the Minhang District Government in Shanghai.

The enantioselective N—H insertion of α-diazoesters and carbamates provides a potentially attractive approach to α-amino acid derivatives. Herein, a novel cooperative catalytic system of achiral dirhodium(Ⅱ) acetates, chiral sulfonamide urea and achiral sulfonic acid was developed for asymmetric N—H insertion reactions. Prochiral ammonium ylide intermediates, generated in situ from α-diazoesters and carbamates initiated by dirhodium(Ⅱ) acetate, underwent asymmetric protonation with a considerable enantioselectivity in the presence of chiral sulfonamide urea and achiral sulfonic acid as co-catalysts. The co-catalysts of chiral sulfonamide urea and achiral sulfonic acid were considered as a chiral proton shuttle assisting the asymmetric proton transfer process to control the enantioselectivity. This methodology provides an efficient and mild approach to α-amino acid derivatives in high yields (up to 84% yield) with moderate enantioselectivity (up to 77% ee).

Key words: N—H insertion, chiral sulfonamide urea, ammonium ylide, co-catalysts, α-amino acid derivatives

Cite this article

Ni Yi, Guo Xin, Hu Wenhao, Liu Shunying. Asymmetric N—H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea[J]. Chin. J. Org. Chem., 2014, 34(1): 107-111.

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[1] (a) Dandekar, T.; Schuster, S.; Snel, B.; Huynen, M.; Bork, P. Biochemistry 1999, 343, 115.

(b) Ronimus, R. S.; Morgan, H. W. Archaea 2003, 1, 199.

[2] Yudin, A. K. Catalyzed Carbon-Heteroatom Bond Formation, Wiley-VCH, Weinheim, 2011.

[3] (a) Salzmann, T. N.; Ratcliffe, R.W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.

(b) Pavlyuk, O.; Teller, H.; McMills, M. C. Tetrahedron Lett. 2009, 50, 2716.

(c) Shi, B.; Blake, A. J.; Lewis, W.; Campbell, B. I.; Judkins, B. D.; Moody, C. J. J. Org. Chem. 2010, 75, 152.

(d) Xu, Q.; Zhao, C.; Zhou, Y.; Yin, S.; Han, L. 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.)

(e) Xie, Y.; Song, R.; Xiang, J.; Li, J. Chin. J. Org. Chem. 2012, 32, 1555 (in Chinese).

(谢叶香, 宋仁杰, 向建南, 李金恒, 有机化学, 2012, 32, 1555.;

f) Liu, Y.; Wang, Z.; Ding, K.-L. Acta Chim. Sinica 2012, 70, 1464 (in Chinese).

(刘龑, 王正, 丁奎岭, 化学学报, 2012, 70, 1464.;

g) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427 (in Chinese).

(谢建华, 周其林, 化学学报, 2012 70, 1427.)

[4] (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998, Chapter 8.

(b) Zhang, Z.-H.; Wang, J.-B. Tetrahedron 2008, 64, 6577.

[5] (a) Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 9148.

(b) Sonia S, S.; Anita, M. E. J. Am. Chem. Soc. 2012, 134, 8798.

(c) Elliott, J. D.; Lin, X.-C.; Ren, F.; Xiang, J.-N.; Yang, Ting; Zhuang, H.; Liu, L.-H. Tetrahedron Lett. 2013, 54, 4159.

[6] (a) Doyle, M. P.; Tamblyn, W. H.; Bagheri, V. J. Org. Chem. 1981, 46, 5094.

(b) Doyle, M. P.; Bagheri, V.; Claxton, E. J. Chem. Soc. 1990, 46.

(c) West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115, 1177.

[7] Yates, P. J. Am. Chem. Soc. 1952, 74, 5376.

[8] Garca, C. F.; McKervey, M. A.; Ye, T. Chem. Commun. 1996, 1465

[9] Saegusa, T.; Y. Ito, S.; Kobayashi, K.; Hirota, T.; Shimizu. Tetrahedron Lett. 1966, 7, 6131.

[10] Nicoud, J. F.; Kagan, H. B. Tetrahedron Lett. 1971, 12, 2065.

[11] Liu, B.; Zhu, S.-F.; Zhang,W.; Chen, C.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 5834.

[12] Lee, E. C.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 12066.

[13] Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986.

[14] Beck, E. M.; Hyde, A. M.; Jacobsen, E. N. Org. Lett. 2011, 13, 4260.

[15] Xu, B.; Zhu, S.-F.; Xie, X.-L.; Shen, J.-J.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 1.

[16] Guo, X.; Hu, W.-H. Acc. Chem. Res. 2014, 46, 2427.

[17] Saito, H.; Morita, D.; Uchiyama, T.; Miyake, M.; Miyairi, S. Tetrahedron Lett. 2012, 53, 6662.

[18] Zhu, S.-F.; Cai, Y.; Mao, H.-X.; Xie, J.-H.; Zhou, Q.-L. Nature Chem. 2010, 2, 546.

[19] Lee, E. C.; Fu, G. C. J. Chem. Soc. 2007, 129, 12066.

[20] Tan, K. L.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 119, 1337.

[21] Katritzky, A. R.; Fedoseyenko, D.; Kima, M. S.; Steel, P. J. Tetrahedron: Asymmetry 2010, 21, 51.

基于醋酸铑、磺酸和手性亚磺酰胺基脲共催化的α-重氮酯与酰胺不对称N—H插入反应研究

Asymmetric N—H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea

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