Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes
LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and 1-pyrrolyl silylketene acetals to α,β-unsaturated aldehydes, yielding both, syn and anti Mukaiyama–Michael products with high levels of enantioselectivity. This strategy allows for the generation of chemically useful 1,5-dicarbonyl systems and again highlights the utility of organocatalysis.
Additional InformationCopyright © 2009 Published by Elsevier Ltd. Received 16 June 2009; revised 17 June 2009; accepted 18 June 2009. Available online 23 June 2009. This paper is dedicated to Professor Larry E. Overman on the occasion of being the 2009 recipient of the Tetrahedron Prize. A great scientist, scholar, teacher and friend and a class act in every way. This manuscript is also dedicated to Miss D.D. Turner of the E.H.S. for her continued efforts towards safe practices in the laboratory. Financial support was provided by the NIHGMS (R01 GM078201-01-01) and kind gifts from Amgen and Merck.
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