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Synlett 2006(12): 1859-1862  
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]

Ulrich Groth*, Christian Kesenheimer, Jürgen Neidhöfer
Fachbereich Chemie, Universität Konstanz, Universitätsstrasse 11, Postfach M-720, 78457 Konstanz, Germany
Fax: +49(7531)884155; e-Mail: ulrich.groth@uni-konstanz.de;
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Publication History

Received 12 April 2006
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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