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
收藏
页码:1957 / 1963
页数:7
相关论文
共 44 条