Enamine‐Mediated Addition of Aldehydes to Cyclic Enones

Abstract

The O-trimethylsilylated alpha,alpha-diphenyl-prolinol-catalyzed addition of aldehydes to cyclic unsaturated enones is described. The apparently unusual stereochemical outcome is discussed

Enantioselective Organocatalyzed Transformations of β-Ketoesters

“…192,194 The nucleophilic enamine derived from diphenyl prolinol organocatalyst 107 256 and the aldehydes acted on the electro-philic site of the β-ketoester moiety (Scheme 101). 407 The bicyclic Aldol products were obtained under Krapcho decarboxylation conditions in 34−86% yields and up to 94% ee.…”

“…Bella and co-workers who pioneered the use of unsaturated β-ketoesters with hydrogen-bonding organocatalysts, extended their methodology to aldehydes using an aminocatalyst. , The nucleophilic enamine derived from diphenyl prolinol organocatalyst 107 and the aldehydes acted on the electrophilic site of the β-ketoester moiety (Scheme ). The bicyclic Aldol products were obtained under Krapcho decarboxylation conditions in 34–86% yields and up to 94% ee.…”