Palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary carbon stereocenter

• Published in: Chemical communications (Cambridge, England) Vol. 48; no. 79; pp. 9936 - 9938
• Main Authors: Shintani, Ryo, Ito, Tomoaki, Nagamoto, Midori, Otomo, Haruka, Hayashi, Tamio
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 11.10.2012
• Subjects: Carbon - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Crystallography, X-Ray; Isocyanates - chemistry; Lactones - chemistry; Ligands; Molecular Conformation; Organophosphorus Compounds - chemistry; Palladium - chemistry; Physical Sciences; Pyrrolidinones - chemistry; Science & Technology; Stereoisomerism; KETENE SILYL ACETAL; ALPHA CONVERTING-ENZYME; GAMMA-LACTAM; (PI-ALLYL)PALLADIUM COMPLEXES; SELECTIVE INHIBITORS; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC-ATTACK; PHOSPHORAMIDITE LIGAND; ENANTIOSELECTIVE CONSTRUCTION; CONJUGATE ADDITION

A palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary stereocenter at the 3-position has been achieved by the reaction of gamma-methylidene-delta-valerolactones with alkyl isocyanates. High enantioselectivity has been realized by employing a newly synthesized chiral phosph...