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anti-selective, catalytic asymmetric vinylogous Mukaiyama Mannich reactions of pyrrole-based silyl dienolates with n-aryl aldimines

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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DOI: 10.1021/jo1021234

Abstract

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.

Item Type:Article
ID Code:5761
Status:Published
Refereed:Yes
Uncontrolled Keywords:Anti-selective, pyrrole-based synil, Mukaiyama Mannich reactions, catalytic asymmetric, VMMnR
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:American Chemical Society
eISSN:1520-6904
Deposited On:11 May 2011 10:02

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