Literature DB >> 21381711

anti-Selective, catalytic asymmetric vinylogous Mukaiyama Mannich reactions of pyrrole-based silyl dienolates with N-aryl aldimines.

Claudio Curti1, Lucia Battistini, Beatrice Ranieri, Giorgio Pelosi, Gloria Rassu, Giovanni Casiraghi, Franca Zanardi.   

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.

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Year:  2011        PMID: 21381711     DOI: 10.1021/jo1021234

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  N-Substituted tertiary and O-substituted quaternary carbon stereogenic centers by site-, diastereo- and enantioselective vinylogous Mannich reactions.

Authors:  Daniel L Silverio; Peng Fu; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Tetrahedron Lett       Date:  2015-04-09       Impact factor: 2.415

  1 in total

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