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Chemistry. 2006 Aug 25;12(25):6506-13. doi: 10.1002/chem.200600334.

Radical-polar crossover domino reactions involving organozinc and mixed organocopper/organozinc reagents.

Chemistry (Weinheim an der Bergstrasse, Germany)

Fabrice Denes, Sabrina Cutri, Alejandro Perez-Luna, Fabrice Chemla

Affiliations

  1. Université Pierre et Marie Curie - Paris 6, Laboratoire de chimie organique (UMR CNRS 7611), Institut de chimie moléculaire (FR 2769) case 183, 4 place Jussieu, 75252 Paris cedex 05, France.

PMID: 16789032 DOI: 10.1002/chem.200600334

Abstract

A domino process involving Michael addition and carbocyclization has been developed starting from beta-N-allylamino enoates and various organometallic reagents (organozinc halides, diorganozinc reagents, and copper/zinc mixed species). In all cases the mechanism of this domino reaction has been evidenced to involve a radical-polar crossover mechanism.

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