Issue 19, 2012
From the journal:

Chemical Communications

One-pot Crabbé homologation-radical cascade cyclisation with memory of chirality†‡

Shovan Mondal,a   Malek Nechab,*a   Nicolas Vanthuyneb  and  Michèle P. Bertrand*a  

* Corresponding authors

a Institut de Chimie Radicalaire (ICR), UMR 7273, Aix-Marseille Université, Faculté de St Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France
E-mail: malek.nechab@univ-provence.fr, michele.bertrand@univ-cezanne.fr

b ISM2, UMR 6263, Aix-Marseille Université, Faculté de St Jérôme, Avenue Normandie-Niemen, 13397 Marseille Cedex 20, France

Abstract

The tandem Crabbé homologation-radical rearrangement of terminal enediynes leads, in a one-pot procedure, to the enantioselective synthesis of six- and seven-membered ring α-aminoesters bearing a quaternary stereocenter based on the phenomenon of memory of chirality.

Graphical abstract: One-pot Crabbé homologation-radical cascade cyclisation with memory of chirality

  • This article is part of the themed collection: Chirality
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Article information

DOI
https://doi.org/10.1039/C2CC17830C
Article type
Communication
Submitted
14 Dec 2011
Accepted
11 Jan 2012
First published
12 Jan 2012

Chem. Commun., 2012,48, 2549-2551

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One-pot Crabbé homologation-radical cascade cyclisation with memory of chirality

S. Mondal, M. Nechab, N. Vanthuyne and M. P. Bertrand, Chem. Commun., 2012, 48, 2549 DOI: 10.1039/C2CC17830C

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