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Synthesis 2003(9): 1419-1426
DOI: 10.1055/s-2003-40191
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

[2+3] Cycloadditions Between Nitroalkenes and Camphor-Derived Oxazoline N-Oxides and Radical Denitration of the Adducts

Arnaud Voituriez, Julien Moulinas, Cyrille Kouklovsky*, Yves Langlois*
Laboratoire de Synthèse Des Substances Naturelles Associé au CNRS, ICMMO, Bâtiment 410, Université de Paris-Sud, 91405 Orsay, France
Fax: +33(1)69154679; e-Mail: cykouklo@icmo.u-psud.fr; e-Mail: langlois@icmo.u-psud.fr;
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Publication History

Received 28 April 2003
Publication Date:
24 June 2003 (online)

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Abstract

[2+3] Cycloadditions between camphor-derived oxazoline N-oxide 2 and nitroalkenes 3a-f afforded stereoselectively adducts 4a-f. Radical denitration followed by acidic hydrolysis gave rise to anti-aldols 8a,b. The radical intermediate was also trapped by a suitable alkene, giving rise to a single stereoisomer.

Key words

cycloaddition - asymmetric synthesis - radical

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15

Scheme 10 Note: this special purification procedure applies when­ever phenyl-substituted nitroalkenes are used in the cycloaddition (Scheme 10).