Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 7, Pages 1037-1040Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600536
Keywords
beta-amino acids; asymmetric catalysis; imines; Mannich reaction; organic catalysis
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We describe a biomimetic organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to imines. This simple protocol makes use of readily available Cinchona-derived organocatalysts and nucleophiles at the carboxylate oxidation state. The resulting P-amino thioesters, being attractive precursors for the preparation of optically active P-amino acids, are formed in good yields and in up to 79% ee. As suggested by several mechanistic insights the desired products are formed via initial formation of a thioester acetate enolate via decarboxylation of the malonic acid half thioester, followed by addition to the imine.
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