Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes

被引：16

作者：

Feroci, M

Inesi, A ^{[1
]}

Palombi, L

Rossi, L

机构：

[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67040 Laquila, Italy

[2] Univ Roma La Sapienza, Dipartimento Ingn Chim Mat Mat Prime & Met, I-00161 Rome, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(01)00385-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A mild and efficient electrochemical alternative to classical base-catalyzed conjugate addition of nitrogen nucleophiles is reported here. The cleavage of the carbamic N . H bond of Evans' chiral auxiliaries can be very efficiently performed by electrolysis under galvanostatic control and the resulting naked anions used for highly, diastereoselective conjugate addition to nitroalkenes. The degree of stereoselectivity was shown to depend on the steric hindrance of the group at the ring C(4) of the starting oxazolidin-2-one. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：2331 / 2335

页数：5

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