Curti, Claudio and Battistini, Lucia and Ranieri, Beatrice and Pelosi, Giorgio and Rassu, Gloria Maria Rita and Casiraghi, Giovanni and Zanardi, Franca (2011) anti-selective, catalytic asymmetric vinylogous Mukaiyama Mannich reactions of pyrrole-based silyl dienolates with n-aryl aldimines. The Journal of Organic Chemistry, Vol. 76 (7), p. 2248-2252. eISSN 1520-6904. Article.
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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.
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