Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 3, Issue 10, Pages 1793-1800Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200800264
Keywords
aldehydes; barium; imines; ketones; propargylation
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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 THE Especially in the case of ketones, the corresponding homopropargylic alcohols form almost exclusively. In the reaction of cc,p-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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