Regio- and stereo-selective γ-substitution of allylic sulphoxides and sulphones with lithium dialkylcuprates. A new synthesis of trisubstituted olefins
作者:Yukio Masaki、Kazuhiko Sakuma、Kenji Kaji
DOI:10.1039/c39800000434
日期:——
A new regio- and stereo-selective γ-substitution of allylic sulphoxides and sulphones with lithium dialkylcuprates providing a promising new method for the preparation of trisubstituted olefins in particular is described.
Cyanomethylenetrimethylphosphorane (CMMP), a new Mitsunobu reagent developed recently by the authors, mediated the alkylation of prenyl and geranyl phenyl sulfone with primary and secondary alcohols quite efficiently. Utilizing geranyl phenyl sulfone, norfaranal, an analog of the unique trail pheromone produced by Pharaoh's ant, was synthesized in a short number of steps. (C) 2001 Elsevier Science Ltd. All rights reserved.
MASAKI, YUKIO;SAKUMA, KAZUHIKO;KAJI, KENJI, J. CHEM. SOC. PERKIN TRANS., 1985, N 6, 1171-1175