DOI: 10.1002/anie.202310436 ISSN:
Asymmetric Allenylation of Alkynes mediated by Chiral Organoselenated Reagents under Oxidative Conditions.
Rongyu Sun, Emilie Viaud, Rajesh Nomula, Jean-Valère Naubron, Nicolas Daugey, Thierry Buffeteau, Frédéric Castet, Patrick Yves Toullec, Stéphane Quideau, Philippe Alexandre Peixoto- General Chemistry
- Catalysis
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.