Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt

K Takai, Y Kunisada, Y Tachibana, N Yamaji…

Index: Takai, Kazuhiko; Kunisada, Yuji; Tachibana, Yukiko; Yamaji, Nana; Nakatani, Emi Bulletin of the Chemical Society of Japan, 2004 , vol. 77, # 8 p. 1581 - 1586

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Citation Number: 14

Abstract

(Diiodomethyl) trimethylsilane (Me 3 SiCHI 2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3 SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1- alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me 3 SiCl, and a catalytic amount of CrCl 3 [thf] 3 in THF. Similarly,(E)-1- alkenylboronic esters are prepared stereoselectively in good to excellent yields by ...