A new organocatalyzed Michael-Michael cascade reaction generates highly substituted fused carbocycles.
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.
McGarraugh
Patrick G
PG
Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, New York 11210, USA.
Brenner
Stacey E
SE
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003503:Cyclobutanes; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003503:Cyclobutanes; D007659:Ketones; D011084:Polycyclic Aromatic Hydrocarbons