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Synlett 1998; 1998(6): 596-598
DOI: 10.1055/s-1998-1738
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Diels-Alder Reactions of α,β-Unsaturated Thioesters and α,β-Unsaturated Selenoesters

Chang-Ho Byeon* , Cheng-Yi Chen, David A. Ellis, David J. Hart, Jing Li
  • *Department of Chemistry, The Ohio State University, 100 W. 18th Ave. Columbus, Ohio 43210, USA
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Publication History

Publication Date:
31 December 2000 (online)

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α,β-Unsaturated thioesters and selenoesters serve as dienophiles in Diels-Alder reactions with a variety of 1,3-dienes. Good levels of regioselectivity are obtained with unsymmetrical dienes when Lewis acid promoters are used. Thioesters and selenoesters are more reactive than the corresponding methyl esters based on competition experiments with cyclopentadiene.

[4+2]-cycloaddition - unsaturated selenoester - unsaturated thioester