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. 2007 Aug 16;9(17):3387-90.
doi: 10.1021/ol071380x. Epub 2007 Jul 26.

Ba-catalyzed direct Mannich-type reactions of a beta,gamma-unsaturated ester providing beta-methyl aza-Morita-Baylis-Hillman-type products

Akitake Yamaguchi  1 , Naohiro Aoyama, Shigeki Matsunaga, Masakatsu Shibasaki
Affiliations

Ba-catalyzed direct Mannich-type reactions of a beta,gamma-unsaturated ester providing beta-methyl aza-Morita-Baylis-Hillman-type products

Akitake Yamaguchi et al. Org Lett. .

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.

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