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A proline-catalyzed asymmetric Robinson annulation reaction

2000; Elsevier BV; Volume: 41; Issue: 36 Linguagem: Inglês

10.1016/s0040-4039(00)01180-1

1873-3581

Tommy Bui, Carlos F. Barbas,

Axial and Atropisomeric Chirality Synthesis

A single-step enantioselective synthesis of the Wieland–Miescher ketone (5) is presented. We show that l-proline as well as a number of other chiral amines can act as catalysts of both steps of the Robinson annulation reaction. Other chiral amines are identified as catalysts of Michael and aldol addition reactions.