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

Yamaguchi, Akitake; Aoyama, Naohiro; Matsunaga, Shigeki; Shibasaki, Masakatsu

Yamaguchi, Akitake; Aoyama, Naohiro; Matsunaga, Shigeki; Shibasaki, Masakatsu.

Afiliación

Yamaguchi A; Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo 7-3-1, Tokyo 113-0033, Japan.

Org Lett ; 9(17): 3387-90, 2007 Aug 16.

Article en En | MEDLINE | ID: mdl-17655253

RESUMEN

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.

Asunto(s)

Bario/química; Ésteres/química; Alquenos/química; Catálisis; Ligandos

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Bario / Ésteres Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2007 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

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