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Bisphosphine-Catalyzed Mixed Double-Michael Reactions: Asymmetric Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines

Vardhineedi Sriramurthy, Gregg A. Barcan and Ohyun Kwon*

*Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Email: ohyunchem.ucla.edu

V. Sriramurthy, G. A. Barcan, O. Kwon, J. Am. Chem. Soc., 2007, 129, 12928-12929.

DOI: 10.1021/ja073754n (free Supporting Information)


Abstract

Bisphosphine-catalyzed mixed double-Michael reactions between amino-acid-derived pronucleophiles as Michael donors and electron-deficient acetylenes as acceptors afford β-amino carbonyl derivatives of oxazolidines, thiozolidines, and pyrrolidines in excellent yields and with high diastereoselectivities under operationally simple and mild conditions.

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proposed mechanism



Key Words

N-Heterocycles, Organocatalysis, Pyrrolidines, Oxazolidines, Thiazolidines


ID: J48-Y2007-3460