RING-OPENING SN2' REACTIONS OF 7-OXANORBORNENES BY ORGANOLITHIUM REAGENTS - REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF SUBSTITUTED CYCLOHEXENEDIOLS

被引：16

作者：

ARJONA, O ^{[1
]}

DELAPRADILLA, RF ^{[1
]}

MARTINDOMENECH, A ^{[1
]}

PLUMET, J ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN GEN,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1990年 / 46卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)81475-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nucleophilic Sn2' bridge opening of 7-oxabicyclo[2.2.1] hept-5-en-2-ols with organolithium reagents occurs in a regio- and stereospecific fashion to produce 6-substituted-cyclohex-4-en-1,3-diols, regardless of the stereochemistry at C-2. A free alcohol functionality is necessary to attain complete regiocontrol of the process. The methodology is utilized to prepare an optically pure cyclohexene derivative, (+)-(1S,3S,6R)-6-n-butyl-3-methyl-cyclohex-4-en-1,3-diol (5b), as a model system. © 1990.

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页码：8187 / 8198

页数：12

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