Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters

被引：8

作者：

Battaglia, A

Baldelli, E

Barbaro, G

Giorgianni, P

Guerrini, A

Monari, M

Selva, S

机构：

[1] CNR, ISOF, I-40129 Bologna, Italy

[2] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(02)00440-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Addition reactions of the chiral lithium (2S)-enolates of the (2S,5S)-2-tert-butyl-5,-methyl-[1,3]dioxolan-4-one and (2S,5S)-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S,5R,1'R)-1'-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1825 / 1832

页数：8

共 39 条

[1] SIR97:: a new tool for crystal structure determination and refinement [J].