Studies on the Cu(I)-Catalyzed Regioselective <i>anti</i>-Carbometallation of Secondary Terminal Propargylic Alcohols
作者:Zhan Lu、Shengming Ma
DOI:10.1021/jo0524021
日期:2006.3.31
A highly regioselective Cu(I)-catalyzed anti-carbometallation of secondary terminal propargylicalcohols with 1° alkyl or aryl Grignard reagents affording 2-substituted allylic alcohols was developed. By using this method, optically active allylic alcohols can be prepared from the optically active propargylicalcohols without obvious loss of the enantiopurity. The cyclic organometallic intermediate
Novel competing reaction of 1-methoxy-2-(trimethylsilyl)-3-hydroxy moiety in base-induced peterson olefination; mechanistic rationale of the reaction
作者:Keiji Yamamoto、Tsuneo Kimura、Yoichi Tomo
DOI:10.1016/s0040-4039(01)81186-2
日期:1984.1
In the base-induced Petersonolefination of diastereomerically pure 8-methoxy-7-(trimethylsilyl)-6-tridecanol, anti pathway to eliminate a methoxide ion was found to compete significantly with amply precedented syn-elimination of a trimethylsilanolate ion. On the basis of an extent of the competing reactions which depend markedly on the respective diastereomers (three from four diastereomers) the detailed