Stereodivergent synthesis of all diastereomers of 4-aminoheptane-3,5-diol from (L)-serine

被引：24

作者：

Andrés, JM ^{[1
]}

Pedrosa, R ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 21期

关键词：

asymmetric synthesis; amino alcohols; amino aldehydes; diastereoselection;

D O I：

10.1016/S0040-4020(98)00232-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the two diasteromeric meso forms of 4-amino-3,5-heptanediol (3R,4r,5S)-1a and (3S,4s,5R)-1b and the two pseudo C-2-symmetric enantiomers (3S,5S)-1c and (3R,5R)-ent-1c is described by stereocontrolled ethylmagnesium bromide or diethylzinc addition to diastereomeric alpha-amino-beta-hydroxy pentanal derivatives 9 and 13. These derivatives were prepared from (2S)-N,N-dibenzyl-O-TBS-serinal 2, that in turn were obtained from (L)-serine. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5607 / 5616

页数：10

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