title: A highly diastereoselective and enantioselective synthesis of polysubstituted pyrrolidines via an organocatalytic dynamic kinetic resolution cascade.
abstract: Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50-95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.
authors.affiliation: Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Cheng
authors.forename: Sixuan
authors.initials: S
authors.lastname: Meng
authors.forename: Yong
authors.initials: Y
authors.lastname: Huang
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D011759:Pyrrolidines