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Synlett 2006(12): 1859-1862
DOI: 10.1055/s-2006-947349
DOI: 10.1055/s-2006-947349
LETTER
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Addition of Organocerium(III) Reagents Derived from 3-Substituted Propargyl Bromides to Aldehydes [1]
Further Information
Received
12 April 2006
Publication Date:
24 July 2006 (online)
Publication History
Publication Date:
24 July 2006 (online)
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Abstract
Various cerium allenyl reagents were generated by transmetallation of allenyl Grignard compounds with CeCl3 and subsequent conversion into homopropargylic alcohols by addition to various aliphatic and aromatic aldehydes. The α-acetylenic alcohols were obtained with regioselectivities and diastereoselectivities up to 98% de in favor of the threo-diastereomers.
Key words
lanthanides - organometallic reagents - addition reactions - diastereoselectivity - regioselectivity
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