Diastereo- and Enantioselective (3 + 2) Cycloaddition of a New Aza-π-Allylpalladium Zwitterionic Intermediate - Archive ouverte HAL
Article Dans Une Revue Journal of Organic Chemistry Année : 2023

Diastereo- and Enantioselective (3 + 2) Cycloaddition of a New Aza-π-Allylpalladium Zwitterionic Intermediate

Résumé

Cycloaddition of azaoxyallyl cations or other C-(C=O)-N synthon precursors is a well-established route towards lactams and other N-heterocycles but, despite the wide synthetic scope of this approach, enantioselective versions remain scarce. We herein report 5-vinyloxazolidine-2,4-diones (VOxD) as a suitable precursor of chiral palladium-aza-oxyallyl intermediates. In the presence of electrophilic alkenes, (3+2) γ-lactam cycloadducts could be formed with high level of diastero-and enantioselectivity.

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Chimie
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Dates et versions

hal-04295618 , version 1 (20-11-2023)

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Anaïs Scuiller, Nicolas Casaretto, Alexis Archambeau. Diastereo- and Enantioselective (3 + 2) Cycloaddition of a New Aza-π-Allylpalladium Zwitterionic Intermediate. Journal of Organic Chemistry, 2023, 88 (14), pp.9941-9945. ⟨10.1021/acs.joc.3c00707⟩. ⟨hal-04295618⟩
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