4.4 Article

Diastereoselective addition of organocerium(III) reagents derived from 3-substituted propargyl bromides to aldehydes

Journal

SYNLETT
Volume -, Issue 12, Pages 1859-1862

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-2006-947349

Keywords

lanthanides; organometallic reagents; addition reactions; diastereoselectivity; regioselectivity

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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 a-acetylenic alcohols were obtained with regioselectivities and diastereoselectivities up to 98% de in favor of the threo-diastereomers.

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