Asymmetric synthesis of 1,3-aminoketals

被引：14

作者：

Bariau, A ^{[1
]}

Canet, JL ^{[1
]}

Chalard, P ^{[1
]}

Troin, Y ^{[1
]}

机构：

[1] Univ Clermont Ferrand, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, F-63174 Aubiere, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 22期

关键词：

D O I：

10.1016/j.tetasy.2005.09.024

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric synthesis of alpha-chiral 1,3-aminoketals 1, useful chiral building blocks for piperidine preparation, was achieved in seven steps involving highly diastereoselective 1,4-addition of Davies' lithium amide to an alpha,beta-unsaturated ester. Problems of partial racernization observed during transformation of the ester moiety into a keto function, via a Weinreb amide, were solved using non-conventional experimental conditions. This procedure allowed the preparation of the title compounds in > 90% enantiomeric excess. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3650 / 3660

页数：11

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