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Selective propargylation of carbonyl compounds and imines with barium reagents.

Authors
  • Yanagisawa, Akira1
  • Suzuki, Takahiro
  • Koide, Takanori
  • Okitsu, Shogo
  • Arai, Takayoshi
  • 1 Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba, Japan. [email protected]
Type
Published Article
Journal
Chemistry - An Asian Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Oct 06, 2008
Volume
3
Issue
10
Pages
1793–1800
Identifiers
DOI: 10.1002/asia.200800264
PMID: 18770517
Source
Medline
License
Unknown

Abstract

A Barbier-type regioselective propargylation of aldehydes and ketones with (3-bromobut-1-ynyl)trimethylsilane has been achieved using reactive barium as a low-valent metal in THF. Especially in the case of ketones, the corresponding homopropargylic alcohols form almost exclusively. In the reaction of alpha,beta-unsaturated carbonyl compounds, only 1,2-adducts have been observed. This method is also applicable to propargylation of imines, and the corresponding homopropargylic amines are obtained regiospecifically in good yields with diastereomeric ratios of up to 87:13.

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