N-Benzyl Aspartate Nitrones: Unprecedented Single-Step Synthesis and [3+2] Cycloaddition Reactions with Alkenes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2008

N-Benzyl Aspartate Nitrones: Unprecedented Single-Step Synthesis and [3+2] Cycloaddition Reactions with Alkenes

Résumé

N-Benzyl aspartate nitrones 2, prepared by addition of N-benzylhydroxylamine to dialkyl acetylenedicarboxylates 1, underwent [3 + 2] thermal cycloaddition with a wide range of alkenes to afford isoxazolidines 4 bearing a polyfunctionalized quaternary center. Under these uncatalyzed conditions, the trans stereocontrol observed with vinyl ethers is higher than that obtained with all acyclic activated nitrones reported to date. The first asymmetric access to a type-4 pure adduct was achieved starting from the chiral aspartate nitrone derived from (S)-α-methylbenzylhydroxylamine.

Domaines

Chimie organique
Fichier non déposé

Dates et versions

hal-00335362 , version 1 (29-10-2008)

Identifiants

Citer

T .B. Nguyen, Arnaud Martel, Robert Dhal, Gilles Dujardin. N-Benzyl Aspartate Nitrones: Unprecedented Single-Step Synthesis and [3+2] Cycloaddition Reactions with Alkenes. Organic Letters, 2008, 10 (20), pp.4493-4496. ⟨10.1021/ol8017243⟩. ⟨hal-00335362⟩

Collections

CNRS UNIV-LEMANS
29 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More