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Synthesis 2006(4): 666-674
DOI: 10.1055/s-2006-926299
DOI: 10.1055/s-2006-926299
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient CuI-Promoted Synthesis of Tri- and Tetrasubstituted Alkenes Using Organozinc Species
Further Information
Received
27 July 2005
Publication Date:
11 January 2006 (online)
Publication History
Publication Date:
11 January 2006 (online)
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Abstract
An efficient method for the synthesis of multifunctionalized alkenes has been developed. In the presence of 5 mol% CuI as catalyst, organozinc species CF3COOZnEt, CF3COOZnMe and CF3COOZnPh reacted with α,β-acetylenic ketones and aldehydes in one pot providing trisubstituted alkenes in high yields with stereoselectivity. The reaction with β-substituted-α,β-acetylenic ketones gave tetrasubstituted alkenes in good yields with Z-isomers as the major products.
Key words
organozinc species - α,β-acetylenic ketones - aldehydes - multifunctionalized alkenes - CuI
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