REGIOSELECTIVE OPENING OF EPOXY ALCOHOLS - MILD CHEMOSELECTIVE AND STEREOSELECTIVE PREPARATION OF IODOHYDRINS AND 1,2-DIOLS

被引：53

作者：

BONINI, C ^{[1
]}

RIGHI, G ^{[1
]}

SOTGIU, G ^{[1
]}

机构：

[1] UNIV ROME LA SAPIENZA,DIPARTMENTO CHIM,ARS,CTR STUDIO CHIM SOSTANZE ORGAN NAT,I-00185 ROME,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 21期

关键词：

D O I：

10.1021/jo00021a045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.

引用

页码：6206 / 6209

页数：4

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