An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols

被引：18

作者：

Dias, Luiz C. ^{[1
]}

Fattori, Juliana ^{[1
]}

Perez, Carla C. ^{[1
]}

de Oliveira, Vanda M. ^{[1
]}

Aguilar, Andrea M. ^{[1
]}

机构：

[1] Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

TETRAHEDRON | 2008年 / 64卷 / 25期

基金：

巴西圣保罗研究基金会;

关键词：

allylsilanes; allylstannanes; catalytic dihydroxylation; aminoketones; sphingolipids; aldol reaction; boron enolates;

D O I：

10.1016/j.tet.2008.04.049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

AWe wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5891 / 5903

页数：13

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