A NOVEL ENTRY INTO WITTIG REARRANGEMENTS - A STEREOSELECTIVE [1,2]-WITTIG REARRANGEMENT WITH INVERSION OF CONFIGURATION AT THE CARBANION CENTER

被引：28

作者：

HOFFMANN, R ^{[1
]}

BRUCKNER, R ^{[1
]}

机构：

[1] UNIV WURZBURG, INST ORGAN CHEM, AM HUBLAND, W-8700 WURZBURG, GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 08期

关键词：

CARBANIONS; CONFIGURATIONAL STABILITY; DIASTEREOSELECTIVITY; 1,2]-WITTIG REARRANGEMENT;

D O I：

10.1002/cber.19921250824

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The O,Se-ketal 10, through lithium naphthalenide induced reductive cleavage of its C(sp3) - Se bond, was converted into the alpha-lithio ether 11a with an equatorially oriented C - O bond. At -78-degrees-C, 11 a undergoes a rapid [1,2]-Wittig rearrangement to provide stereoselectively the homoallylic alcohol 12a with an axial OH group. Thus, the rearrangement proceeds with inversion of configuration at the carbanion center.

引用

页码：1957 / 1963

页数：7

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