The First Organocatalysed Direct
Aldol Reaction of 2-Hydroxycyclobutanone

David J. Aitken; Francesca Capitta; Angelo Frongia; Didier Gori; Régis Guillot; Jean Ollivier; Pier Paolo Piras; Francesco Secci; Marco Spiga

doi:10.1055/s-0030-1259550

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Synlett 2011(5): 712-716
DOI: 10.1055/s-0030-1259550

LETTER

The First Organocatalysed Direct Aldol Reaction of 2-Hydroxycyclobutanone

David J. Aitken^a, Francesca Capitta^a,b, Angelo Frongia*^a,b, Didier Gori^a, Régis Guillot^a, Jean Ollivier*^a, Pier Paolo Piras^b, Francesco Secci^b, Marco Spiga^b
^a Laboratoire de Synthèse Organique et Méthodologie, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d"Orsay, Université Paris-Sud 11, 91405 Orsay, France
e-Mail: jean.ollivier@u-psud.fr;
^b Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S 554, Bivio per Sestu, 09042, Monserrato, Italy
Fax: +39(070)6754388; e-Mail: angelo.frongia@gmail.com;

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Publikationsverlauf

Received 16 December 2010
Publikationsdatum:
11. Februar 2011 (online)

Abstract
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Abstract

l-Tryptophan has been shown to catalyse the enantioselective aldol reaction between 2-hydroxycyclobutanone and an aromatic aldehyde in DMF solution. The reaction is completely regioselective and gives the 2,2-disubstituted cyclobutanone in up to 80% yield. The major adduct is obtained with ee values up to 67%, and has an anti relative configuration which contrasts with the selectivity of organocatalysed aldol reactions conducted on acyclic hydroxyacetone substrates.

Key words

cyclobutanone - tryptophan - organocatalysis - aldol reaction - stereoselective reaction.

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