Asymmetric indium-mediated synthesis of homopropargylic alcohols

A method for the enantioselective synthesis of homopropargylic alcohols using indium under Barbier-like conditions is reported herein. Both aromatic and aliphatic aldehydes were successfully converted to the corresponding homopropargylic alcohols in good yield and high enantiomeric excesses using pr...

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Bibliographic Details
Published in:Tetrahedron letters 2006-07, Vol.47 (29), p.5173-5176
Main Authors: Hirayama, Lacie C., Dunham, Kevin K., Singaram, Bakthan
Format: Article
Language:English
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Summary:A method for the enantioselective synthesis of homopropargylic alcohols using indium under Barbier-like conditions is reported herein. Both aromatic and aliphatic aldehydes were successfully converted to the corresponding homopropargylic alcohols in good yield and high enantiomeric excesses using propargyl bromide, indium, and (1 S,2 R)-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.05.049