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Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2021

Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions

Résumé

Under basic conditions and heat, ynamides can serve as precursor to ketenimines, whose synthetic potential is often hampered by their difficulty of access. Herein, we report that they can undergo a [3+2] cycloaddition with 2azaallyl anions, obtained from benzylimines under the same reaction conditions. This reaction between two highly reactive intermediates, both generated in situ from bench stable starting materials, gives access to various nitrogenrich heterocycles. The reaction usually proceeds with excellent diastereoselectivity, in favor of the cis adduct. Deuteration experiments and DFT calculations helped rationalize the regio-and stereo-selectivity of the process as well as the formation of side-products.

Domaines

Chimie organique
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hal-03227971 , version 1 (17-05-2021)

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Paternité - Pas d'utilisation commerciale - Pas de modification

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Agathe C A d'Hollander, Eugénie Romero, Kamsana Vijayakumar, Camille Le Houérou, Pascal Retailleau, et al.. Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions. Advanced Synthesis and Catalysis, 2021, 363 (11), pp.2903-2908. ⟨10.1002/adsc.202100047⟩. ⟨hal-03227971⟩
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