Issue 34, 2005
From the journal:

Chemical Communications

Mechanistic subtleties in the cyclopentannelation of allenolate allyl carbamates: the origin of the center-to-center chirality transfer†

Olalla Nieto Faza,a   Carlos Silva López,a   Rosana Álvareza  and  Ángel R. de Lera*a  

* Corresponding authors

a Dpto. de Química Orgánica, Universidade de Vigo, Lagoas-Marcosende, Vigo, Spain
E-mail: qolera@uvigo.es
Fax: 34 986811940
Tel: 34 986812316

Abstract

The stereospecific rearrangement of allene carbamates i to alkylidenecyclopentenones iii is concerted, displays charge donation from the π*allenonate to the σ*C-leaving group, and shows mechanistic features of both pericyclic and ionic processes, modulated in part by the degree of ionic interaction (O−…Li+) in the putative intermediate allenolate ii.

Graphical abstract: Mechanistic subtleties in the cyclopentannelation of allenolate allyl carbamates: the origin of the center-to-center chirality transfer

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Article information

DOI
https://doi.org/10.1039/B506601H
Article type
Communication
Submitted
12 May 2005
Accepted
27 Jun 2005
First published
27 Jul 2005

Chem. Commun., 2005, 4285-4287

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Mechanistic subtleties in the cyclopentannelation of allenolate allyl carbamates: the origin of the center-to-center chirality transfer

O. N. Faza, C. S. López, R. Álvarez and Á. R. de Lera, Chem. Commun., 2005, 4285 DOI: 10.1039/B506601H

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