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Synlett 2011(8): 1113-1116  
DOI: 10.1055/s-0030-1259933
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins

Thivisha Rajagopal, William W. Ogilvie*
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, ON, K1N 6N5, Canada
Fax: +1(613)5625170; e-Mail: wogilvie@uottawa.ca;
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Publication History

Received 16 February 2011
Publication Date:
30 March 2011 (online)

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Abstract

The generation of a series of trisubstituted olefins bearing alkyl substituents is described using a stereoselective and regio­selective addition to alkynyl esters. The method produces trisubstituted olefins as single isomers using a convenient and mild transformation in which alkyl boranes are cross-coupled with alkynyl esters and amides using palladium catalysis.

Key words

olefination - stereoselectivity - regioselectivity - cross-coupling - asymmetric synthesis

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