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Synlett 2011(5): 712-716  
DOI: 10.1055/s-0030-1259550
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The First Organocatalysed Direct Aldol Reaction of 2-Hydroxycyclobutanone

David J. Aitkena, Francesca Capittaa,b, Angelo Frongia*a,b, Didier Goria, Régis Guillota, Jean Ollivier*a, Pier Paolo Pirasb, Francesco Seccib, Marco Spigab
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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Publication History

Received 16 December 2010
Publication Date:
11 February 2011 (online)

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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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17

Very recently it was reported that l-Trp did not catalyse the aldol reaction of hydroxyacetone with 4 in water, see ref. 16a.

18

CCDC 772896 contains the supplementary crystallographic data for anti-4. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.