STEREOSELECTIVE GENERATION OF 1,3-DIOXY-SUBSTITUTED AND 1,4-DIOXY-SUBSTITUTED CARBANIONS BY SPARTEINE-ASSISTED DEPROTONATION OF CHIRAL PRECURSORS - SUBSTRATE OR REAGENT CONTROL IN THE SYNTHESIS OF ALPHA,GAMMA-DIOLS AND ALPHA,DELTA-DIOLS

被引：34

作者：

AHRENS, H ^{[1
]}

PAETOW, M ^{[1
]}

HOPPE, D ^{[1
]}

机构：

[1] UNIV KIEL,INST ORGAN CHEM,OLSHAUSENSTR 40-60,W-2300 KIEL 1,GERMANY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 37期

关键词：

CHIRAL; 1-OXYCARBANIONS; ENANTIOSELECTIVE DEPROTONATION; (-)-SPARTEINE;

D O I：

10.1016/S0040-4039(00)79084-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The deprotonation of a dicarbamate, derived from (S)-butane-1,3-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA), respectively. The (S)-pentane-1,4-diol derivative shows the same stereochemical preference under both conditions.

引用

页码：5327 / 5330

页数：4

共 17 条

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