Vinyl-aziridines and cyclopropanes in Pd-catalyzed (3+2)-cycloaddition reactions with cyclic N-sulfonyl imines

• Published in: Tetrahedron Vol. 74; no. 45; pp. 6497 - 6511
• Main Authors: Spielmann, Kim, Tosi, Eleonora, Lebrun, Aurélien, Niel, Gilles, van der Lee, Arie, de Figueiredo, Renata Marcia, Campagne, Jean-Marc
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.11.2018; Elsevier
• Subjects: (3+2)-cycloaddition reactions; catalytic activity; Chemical Sciences; chemical structure; Chemistry; Chemistry, Organic; Cyclic N-sulfonyl imines; cycloaddition reactions; derivatization; diastereoselective synthesis; enantioselectivity; ethyleneimine; imines; Organic chemistry; palladium; Palladium-catalysis; Physical Sciences; pyrrolidines; Science & Technology; Tetrasubstituted carbon; Vinyl-aziridines and cyclopropanes; zwitterions; Tetrasubstituted carbon; Cyclic N-sulfonyl imines; Vinyl-aziridines and cyclopropanes; (3+2)-cycloaddition reactions; Palladium-catalysis; ENANTIOSELECTIVE SYNTHESIS; NITROGEN-HETEROCYCLES; ALPHA,BETA-UNSATURATED ALDEHYDES; STEREOSPECIFIC SYNTHESIS; DEAROMATIVE 3+2 CYCLOADDITION; RING-OPENING CYCLIZATION; DIASTEREOSELECTIVE SYNTHESIS; SYNERGISTIC CATALYSIS; PARA-QUINONE METHIDES; KINETIC ASYMMETRIC TRANSFORMATIONS

Efficient palladium-catalyzed (3 + 2)-cycloaddition reactions of cyclic N-sulfonyl imines and vinyl-aziridines (or cyclopropanes) have been achieved. The reactions, with either vinylic substrate, proceed with excellent yields affording highly functionalized imidazolidine and pyrrolidine derivatives....