American Chemical Society
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anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines

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posted on 2011-04-01, 00:00 authored by Claudio Curti, Lucia Battistini, Beatrice Ranieri, Giorgio Pelosi, Gloria Rassu, Giovanni Casiraghi, Franca Zanardi
Pyrrole-based silyl dienolates undergo asymmetric vinylogous Mukaiyama Mannich reactions with a series of N-aryl aldimines in the presence of the Hoveyda−Snapper amino acid-derived silver(I) catalysts. The Mannich productsα,β-unsaturated δ-amino-γ-butyrolactamsare typically obtained in high yields, excellent γ-site selectivities and anti-diastereoselectivities, and up to 80% enantioselectivity.