Asymmetric 1,3-dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine |
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| Authors: | Florence Chung Mohamed Seltki Laurent Micouin |
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| Institution: | a Laboratoire de Chimie Thérapeutique, UMR 8638 Associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, 75270 Paris cedex 06, France
b Laboratoire de Cristallographie et RMN Biologiques (UMR 8015 CNRS), Facultè des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, 75270 Paris cedex 06, France |
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| Abstract: | The reactivity of a chiral nonracemic glyoxylic azomethine imine has been investigated. This species reacts with a wide range of dipolarophiles, with a complete regio- and facial stereoselectivity. The introduction of an electron-withdrawing substituent on the ylide leads to a lower endo selectivity with electron-withdrawing dipolarophiles, but to an improved exo selectivity with styrene derivatives when compared to the reactivity of aliphatic- or aromatic-substituted ylides. |
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| Keywords: | Cycloadditions Azomethine imine Asymmetric synthesis |
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