Synthesis 2002(1): 0099-0103
DOI: 10.1055/s-2002-19297
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Method for the Synthesis of Terminal (E)-1,3-Dienes

Yong Wang, F. G. West*
Department of Chemistry, University of Utah, 315 S. 1400 East, Rm. 2020, Salt Lake City, UT 84112-0850, USA
Fax: +1(801)5818433; e-Mail: west@chemistry.utah.edu;
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Publikationsverlauf

Received 22 August 2001
Publikationsdatum:
04. August 2004 (online)

Abstract

Lithiated allylic phosphonates undergo efficient olefination reactions with a variety of aldehydes in the presence of HMPA to give terminal 1,3-dienes with high selectivity for the E-isomer. This method is general and procedurally simple.

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While this work was underway, Schlosser and Liu reported a highly stereoselective synthesis of (E)-1,3-dienes with allylphosphonates. [15] However, experimental details were not provided for the optimized conditions using unsubstituted diethyl allylphosphonate with the straight-chain aldehyde nonanal (NaH activated with LiAlH4), and we could not consistently reproduce the reported results (74% yield, 99:1 E/Z).