Literature DB >> 19673513

Crossed intramolecular Rauhut-Currier-type reactions via dienamine activation.

Eugenia Marqués-López1, Raquel P Herrera, Timo Marks, Wiebke C Jacobs, Daniel Könning, Renata M de Figueiredo, Mathias Christmann.   

Abstract

The intramolecular Rauhut-Currier reaction creates a carbon-carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we investigate a novel strategy that involves the formation of electron rich dienamines as key intermediates. Our methodology provides an efficient entry to the iridoid framework.

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Year:  2009        PMID: 19673513     DOI: 10.1021/ol901614t

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis.

Authors:  Giorgio Bencivenni; Patrizia Galzerano; Andrea Mazzanti; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Proc Natl Acad Sci U S A       Date:  2010-06-21       Impact factor: 11.205

2.  Conversion of substrate analogs suggests a Michael cyclization in iridoid biosynthesis.

Authors:  Stephanie Lindner; Fernando Geu-Flores; Stefan Bräse; Nathaniel H Sherden; Sarah E O'Connor
Journal:  Chem Biol       Date:  2014-10-23

3.  Old tricks, new dogs: organocatalytic dienamine activation of α,β-unsaturated aldehydes.

Authors:  Vanesa Marcos; José Alemán
Journal:  Chem Soc Rev       Date:  2016-11-02       Impact factor: 54.564

4.  Lewis acid-catalyzed asymmetric reactions of β,γ-unsaturated 2-acyl imidazoles.

Authors:  Tengfei Kang; Liuzhen Hou; Sai Ruan; Weidi Cao; Xiaohua Liu; Xiaoming Feng
Journal:  Nat Commun       Date:  2020-08-03       Impact factor: 14.919

  4 in total

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