Ba-Catalyzed Direct Mannich-Type Reactions of a β,γ-Unsaturated Ester Providing β-Methyl aza-Morita−Baylis−Hillman-Type Products
- 26 July 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (17), 3387-3390
- https://doi.org/10.1021/ol071380x
Abstract
Barium-catalyzed direct Mannich-type reactions of a beta,gamma-unsaturated ester are described. The Ba-catalyst not only promoted the Mannich-type reactions, but also isomerized Mannich adducts to afford beta-methyl aza-Morita-Baylis-Hillman-type products in 61-88% yield from various aryl, heteroaryl, and alkyl imines. Preliminary trials on enantioselective variants with a chiral biaryldiol ligand gave products in up to 80% ee.Keywords
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