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Synthesis 2007(5): 719-724  
DOI: 10.1055/s-2007-965894
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Aldolization with N-Phenylselanylacetyl Derivatives

Xavier Franck*, Emilie Langlois, Francis Outurquin
UMR-CNRS 6014, Laboratoire d’Hétérochimie Organique de l’IRCOF, Université de Rouen, 1, rue Tesnière, 76131 Mont Saint Aignan, France
Fax: +33(2)35522959; e-Mail: xavier.franck@insa-rouen.fr;
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Publikationsverlauf

Received 2 November 2006
Publikationsdatum:
18. Januar 2007 (online)

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Abstract

The asymmetric introduction of the phenylselanyl moiety using chiral N-phenyselanylacetyloxazolidin-2-thiones and -thiazolidin-2-thiones is reported. The diastereoselectivity is complete in favor of the syn isomer and the aldols so obtained are valuable intermediates for the synthesis of more functionalized molecules such as amino alcohols, after chemoselective activation of the selenium and substitution by nucleophilic nitrogen.

Key words

aldol reaction - selenium - chiral auxiliaries - asymmetric synthesis

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