Regioselective Propargylation of Carbonyl Compounds with (3-Bromoprop-1-ynyl)trimethylsilane Promoted by Reactive Barium

Akira Yanagisawa; Shogo Okitsu; Takayoshi Arai

doi:10.1055/s-2005-869874

LETTER

Regioselective Propargylation of Carbonyl Compounds with (3-Bromoprop-1-ynyl)trimethylsilane Promoted by Reactive Barium

Akira Yanagisawa*^a, Shogo Okitsu^b, Takayoshi Arai^a
^a Department of Chemistry, Faculty of Science, Chiba University, Inage, Chiba 263-8522, Japan
Fax: +81(43)2902789; e-Mail: ayanagi@scichem.s.chiba-u.ac.jp;
^b Graduate School of Science and Technology, Chiba University, Inage, Chiba 263-8522, Japan

Abstract

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Abstract

A Barbier-type propargylation of aldehydes with (3-bromoprop-1-ynyl)trimethylsilane has been achieved using reactive barium as a low-valent metal in THF. This process is effective also for obtaining the desired homopropargylic alcohols in high yields from the corresponding ketones including enolizable ketones such as cyclopent-2-enone.

Key words

barium - propargylation - aldehydes - regioselectivity - ketones

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References

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