Diastereoselective Cycloadditions of Chiral Non-racemic Azomethine Imines

Fanny Roussi; Ariane Chauveau; Martine Bonin; Laurent Micouin; Henri-Philippe Husson

doi:10.1055/s-2000-6311

Synthesis 2000; 2000(8): 1170-1179
DOI: 10.1055/s-2000-6311

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Diastereoselective Cycloadditions of Chiral Non-racemic Azomethine Imines

Fanny Roussi^* , Ariane Chauveau, Martine Bonin, Laurent Micouin, Henri-Philippe Husson

^*Laboratoire de Chimie Thérapeutique Associé au CNRS (UMR 8638) et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 Av. de l'Observatoire, 75270 Paris Cedex 06, France; Fax +33 (01) 43 29 14 03; E-mail: Husson@pharmacie.univ-paris5.fr

Abstract

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(5R)-5-Phenyl[1,3,4]oxadiazinan-2-one (6) is an easily available building block and acts as a chiral non-racemic precursor for azomethine imines. The ylid can be formed regioselectively with various aldehydes and reacts in an efficient manner with a wide range of dipolarophiles. The regio- and diastereoselectivity of the cycloadditions have been fully investigated and can lead, in the best cases, to the creation of three contiguous asymmetric centers in a single step, with complete control of relative and absolute configurations.

azomethine imines - cycloadditions - phenylglycinol - asymmetric synthesis - cyclic hydrazines

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