Issue 26, 2012
From the journal:

Organic & Biomolecular Chemistry

Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones†

David J. Aitken,a   Angela M. Bernard,b   Francesca Capitta,ab   Angelo Frongia,*b   Régis Guillot,a   Jean Ollivier,a   Pier Paolo Piras,*b   Francesco Seccib  and  Marco Spigab  

* Corresponding authors

a Laboratoire de Synthèse Organique et Méthodologie, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO – CNRS UMR 8182), Université Paris-Sud 11, 15 rue Georges Clemenceau, 91405 Orsay, France

b Dipartimento di Scienze Chimiche, Università degli studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, I-09042, Monserrato, Cagliari, Italy
E-mail: afrongia@unica.it, pppiras@unica.it

Abstract

N-Phenylsulfonyl (S)-proline catalyzes the direct aldol reaction of 3-substituted cyclobutanones and aryl aldehydes in good yield and with excellent diastereoselectivity and enantioselectivity. This desymmetrization process provides highly functionalized cyclobutanones with control over three contiguous stereogenic centers.

Graphical abstract: Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones

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Article information

DOI
https://doi.org/10.1039/C2OB25813G
Article type
Paper
Submitted
27 Apr 2012
Accepted
03 May 2012
First published
03 May 2012

Org. Biomol. Chem., 2012,10, 5045-5048

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Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones

D. J. Aitken, A. M. Bernard, F. Capitta, A. Frongia, R. Guillot, J. Ollivier, P. P. Piras, F. Secci and M. Spiga, Org. Biomol. Chem., 2012, 10, 5045 DOI: 10.1039/C2OB25813G

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