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

Supporting Info

Vardhineedi Sriramurthy, Gregg A. Barcan, and Ohyun Kwon*

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

J. Am. Chem. Soc., 2007, 129 (43), pp 12928–12929

DOI: 10.1021/ja073754n

Publication Date (Web): October 9, 2007

Abstract

Bisphosphine-catalyzed mixed double-Michael reactions have been developed to afford β-amino carbonyl derivatives of oxazolidines, thiozolidines, and pyrrolidines in excellent yields and with high diastereoselectivities. Efficient reactions between amino-acid-derived pronucleophiles, such as β-amino alcohols, β-amino thiols, and γ-amino diesters, as Michael donors and electron-deficient acetylenes, such as propiolates, acetylacetylene, and tosylacetylene, as Michael acceptors provided access to azolidines containing both diversity of substituents and asymmetry. This methodologythe first examples of mixed double-Michael reactions of acetylenesis operationally simple and involves mild conditions. Mechanistically, it constitutes a rare example of the anchimeric assistance of bisphosphines in organocatalysis.

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