The first asymmetric synthesis of 1,4-dideoxy-1,4-imino-D-talitol

被引：16

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, Inst Catalysis, Inst Ciencia Mat Aragon,Dept Quim Organ, Zaragoza 50009, Spain

来源：

SYNLETT | 2005年 / 11期

关键词：

stereoselective synthesis; alkaloids; addition reactions; metathesis; dihydroxylations;

D O I：

10.1055/s-2005-871534

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first stereoselective synthesis of 1,4-dideoxy- 1,4-imino-D-Talitol has been achieved in 24% overall yield from conveniently protected (S)-glyceraldimine (1), which is easily prepared from inexpensive D-mannitol. The synthesis is based on the addition of vinylmagnesium bromide to this N-benzylimine followed by N-acylation, ring-closing metathesis and asymmetric dihydroxylation. In this synthesis as many as three stereogenic centres are constructed with total stereoselectivity.

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收藏

页码：1734 / 1736

页数：3

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