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通过使用氮杂芳基磺酰基金鸡纳生物碱酰胺实现丙二酸半硫酯与环状N-磺酰基酮亚胺的有机催化对映选择性脱羧反应。

Organocatalytic enantioselective decarboxylative reaction of malonic acid half thioesters with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides.

作者信息

Nakamura Shuichi, Sano Masahide, Toda Ayaka, Nakane Daisuke, Masuda Hideki

机构信息

Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan).

出版信息

Chemistry. 2015 Mar 2;21(10):3929-32. doi: 10.1002/chem.201406270. Epub 2015 Jan 22.

Abstract

The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation.

摘要

通过使用氮杂芳基磺酰基金鸡纳生物碱酰胺,丙二酸半硫酯(MAHTs)与环状N-磺酰基酮亚胺发生有机催化对映选择性脱羧曼尼希反应,得到了具有高对映选择性的产物。使用假对映体手性催化剂可以得到产物的两种对映体。该反应在脱羧之前通过MAHTs对酮亚胺的亲核加成进行。

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