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Synfacts 2008(11): 1210-1210  
DOI: 10.1055/s-0028-1083468
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Stereospecific Synthesis of Allenes from Propargylic Alcohols

Contributor(s): Paul Knochel, Tobias Thaler
X. Pu, J. M. Ready*
University of Texas Southwestern Medical Center, Dallas, USA
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

A direct straightforward route to the stereospecific synthesis of allenes from propargylic alcohols has been disclosed. Hereby, two complementary sets of conditions have been identified which, together, allow the preparation of dialkyl-, diaryl- and aryl-,alkyl-substituted allenes. The reaction proceeds via syn-addition of the Schwartz reagent to the triple bond of the propargylic alcohol. Subsequent syn-elimination leads to the desired allenes.