Asymmetric synthesis of N-protected syn and anti (E)-3-amino-2-hydroxy-4-hexenoate:: A practical method for the C-α epimerization of anti β-amino-α-hydroxy acids

被引：20

作者：

Brackenridge, I

Davies, SG

Fenwick, DR

Ichihara, O

Polywka, MEC

机构：

[1] Oxford Asymmetry Int PLC, Abingdon OX14 4SD, Oxon, England

[2] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(98)01051-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method to convert anti beta-amino-alpha-hydroxy acids into the corresponding syn esters via the DCC/DMAP . HCl mediated esterification was devised, and methyl (2R,3S)-(E)-3-t-butoxycarbonylamino-2-hydroxy-4-hexenoate 15 was synthesised from the corresponding (2S,3S)-isomer 9 using the epimerization procedure developed. The alpha- and beta-stereogenic centres of 9 were constructed by the Michael addition of a homochiral lithium amide to t-butyl sorbate and subsequent oxidation of the enolate intermediate in one pot. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：533 / 540

页数：8

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