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
收藏
页码：5891 / 5903
页数：13
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