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Synfacts 2008(1): 0071-0071  
DOI: 10.1055/s-2007-991476
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions

Contributor(s): Mark Lautens, Praew Thansandote
A. D. Melhado, M. Luparia, F. D. Toste*
University of California, Berkeley, USA
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

The authors have developed the first enantioselective reaction of azalactones with alkenes to provide D 1-pyrrolines using a chiral gold(I)-SEGPHOS catalyst. A range of electron-deficient alkenes and azalactones are compatible with the reaction and good to excellent diastereoselectivity, regioselectivity, and enantioselectivity (exclusively exo adduct) were observed. Increasing the steric bulk of the azalactone substituents requires switching of the solvent from PhF to a THF-PhF solvent mixture for increased yields.