Stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline

被引：40

作者：

Madhan, A ^{[1
]}

Rao, BV ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 30期

关键词：

imine; Grignard reaction; N-allylation; ring-closing metathesis; dihydroxylation; azasugars;

D O I：

10.1016/S0040-4039(03)01366-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：5641 / 5643

页数：3

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