Ba-catalyzed direct Mannich-type reactions of a beta,gamma-unsaturated ester providing beta-methyl aza-Morita-Baylis-Hillman-type products.
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.
Yamaguchi
Akitake
A
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo 7-3-1, Tokyo 113-0033, Japan.
Aoyama
Naohiro
N
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000475:Alkenes / Q000737:chemistry; D001464:Barium / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D008024:Ligands
D000475:Alkenes; D004952:Esters; D008024:Ligands; D001464:Barium