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Communication

Stable Tetravalent Phosphonium Enolate Zwitterions

Supporting Info

Xue-Feng Zhu, Christopher E. Henry, and Ohyun Kwon*

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569

J. Am. Chem. Soc., 2007, 129 (21), pp 6722–6723

DOI: 10.1021/ja071990s

Publication Date (Web): May 8, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Three-component coupling reactions between trialkylphosphines, methyl propiolates, and aldehydes produced 1:1:1 dipolar adducts in moderate to excellent yields. The product phosphonium enolate zwitterions were isolated as crystalline solids. X-ray crystallographic analyses of these single crystals established unequivocally the dipolar structures of these tetravalent phosphonium enolate zwitterions. Because phosphonium enolates are the first key intermediates in the nucleophilic phosphine-mediated catalysis of α,β-unsaturated carbonyl compounds, this study provides crucial insight into the mechanisms of Morita−Baylis−Hillman-type reactions.

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