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Asymmetric Allenylation of Alkynes mediated by Chiral Organoselenated Reagents under Oxidative Conditions |
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| Authors: | Rongyu Sun Emilie Viaud Dr. Rajesh Nomula Dr. Jean-Valère Naubron Dr. Nicolas Daugey Dr. Thierry Buffeteau Prof. Frédéric Castet Prof. Patrick Y. Toullec Prof. Stéphane Quideau Dr. Philippe A. Peixoto |
| Affiliation: | 1. Univ. Bordeaux, ISM (CNRS–UMR 5255), 351 cours de la Libération., 33405 Talence Cedex, France;2. Aix-Marseille Univ, CNRS, Centrale Marseille, FSCM, Marseille, France;3. Univ. Bordeaux, ISM (CNRS–UMR 5255), 351 cours de la Libération., 33405 Talence Cedex, France Institut Universitaire de France, 1 rue Descartes., 75231 Paris Cedex 05, France |
| Abstract: | The reactivity of novel chiral lactamide-substituted diselenide-based reagents under oxidative conditions was exploited to develop a metal-free method for the preparation of enantioenriched allenylamides from simple alkynes in good yields, and with enantiomeric excesses up to 99 %. The key of the success in this method is attributed to the hydrogen-bonded lactamide appendages that ensure configurational stability of chiral vinyl selenoxide intermediates for an optimal enantiotopic β-syn-elimination step. |
| Keywords: | Allenes Asymmetric Synthesis Chiral Diselenides Selenoxides |