• Organic letters · Dec 2009

    A new organocatalyzed Michael-Michael cascade reaction generates highly substituted fused carbocycles.

    • Patrick G McGarraugh and Stacey E Brenner.
    • Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, New York 11210, USA.
    • Org. Lett. 2009 Dec 17; 11 (24): 5654-7.

    AbstractWhile beta-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using alpha,beta-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using beta-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated in a single step in up to 87% yield and 99% ee.

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