Efficient stereodivergent synthesis of 1,4-dideoxy-1,4-iminohexitols from an (S)-glyceraldimine

被引：26

作者：

Badorrey, R ^{[1
]}

Cativiela, C ^{[1
]}

Díaz-de-Villegas, MD ^{[1
]}

Díez, R ^{[1
]}

Gálvez, JA ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, Fac Ciencias, Inst Ciencia Mat Aragon,Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 04期

关键词：

asymmetric synthesis; imines; asymmetric dihydroxylation; ring-closing metathesis;

D O I：

10.1016/j.tetlet.2003.11.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereodivergent synthesis of 1,4-dideoxy-1,4-iminO-D-mannitoI I and D-allitol III from an (S)-glyceraldimine, which is easily prepared from D-mannitol, has been achieved with overall yields of 62 and 49%, respectively. The synthesis is based on the addition of vinylmagnesium bromide to N-benzylimine 1, derived from readily available (R)-2,3-O-isopropylideneglyceraidehyde, followed by N-allylation or N-acryloylation, ring-closing metathesis and asymmetric dihydroxylation. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：719 / 722

页数：4

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