A New Organocatalyzed Michael−Michael Cascade Reaction Generates Highly Substituted Fused Carbocycles
Organic Letters2009Vol. 11(24), pp. 5654–5657
Citations Over TimeTop 10% of 2009 papers
Abstract
While 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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