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

Kazuhiko Takai, Yuji Kunisada, Yukiko Tachibana, Nana Yamaji, Emi Nakatani

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

(Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, 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 treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR) 2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.

Original languageEnglish
Pages (from-to)1581-1586
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number8
DOIs
Publication statusPublished - Aug 1 2004

ASJC Scopus subject areas

  • Chemistry(all)

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