Synthesis, reactivity and stereochemistry of new phosphorus heterocycles with 5- or 6-membered rings |
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Authors: | Henri-Jean Cristau David Virieux Jérôme Monbrun Yves-Alain Bekro |
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Institution: | a Laboratoire de Chimie Organique, UMR 5076 CNRS, Ecole Nationale Supérieure de Chimie de Montpellier, 8, Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France b Department of Chemistry, Palangkaraya University, Jalan Yos Sudarso, Palangkaraya 73112, Indonesia c Universitéd’Abobo-Adjamé, 02BP801, Abidjan 02, République de Côte d’Ivoire |
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Abstract: | Syntheses of novel phosphorus heterocycles containing α-amino or α-hydroxyphosphonic or phosphinic acids motifs are developed. 2,3-dihydro-1,3-oxaphospholes (1) and 1,4,2-oxazaphosphinanes (2) exhibit a reactive part, respectively the enolether moiety and the P-H bond, which allows various structural modifications: (i) for 1a, by introduction of amino substituents, (ii) for 2a, by hydroxy- or aminoalkylation, by Michael addition or by P-arylation. These reactions present generally a good or even an excellent kinetic diastereoselectivity which can often be predicted by molecular models of the transition states. |
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Keywords: | Phosphorus heterocycles 1 3-oxaphosphole 1 4 2-oxazaphosphinane Stereoselective synthesis |
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