Palladium-catalyzed intramolecular allylic alkylation of α-sulfinyl carbanions: a new asymmetric route to enantiopure γ-lactams

• Published in: Tetrahedron letters Vol. 51; no. 11; pp. 1459 - 1461
• Main Authors: Vogel, Sophie, Bantreil, Xavier, Maitro, Guillaume, Prestat, Guillaume, Madec, David, Poli, Giovanni
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.03.2010; Elsevier
• Subjects: Allylic alkylation; Catalysis; Chemistry; Chemistry, Organic; Enantioselective; Lactam; Palladium; Physical Sciences; Science & Technology; Sulfoxide; Sulfoxide; Allylic alkylation; Palladium; Enantioselective; Catalysis; Lactam; OXIDATION; LIGANDS; SULFIDES; CARBONYL-COMPOUNDS; SULFONES; ALLYLATIONS

A simple and efficient protocol for the intramolecular palladium-catalyzed allylic alkylation of α-sulfinyl carbanions is reported. The use of unsaturated amides bearing a sulfinyl group of defined absolute configuration in concomitance with enantiopure BINAP as the ligand in a biphasic medium provi...