title: Asymmetric Synthesis of (2S,3S)-α-(1-Oxoisoindolin-3-yl)glycines under Low-Basicity "Kinetic" Control.
abstract: The previously illusive (2S,3S)-configured α-(1-oxoisoindolin-3-yl)glycines can be prepared under mild DBU-catalyzed, low-basicity conditions. The overall process includes a cascade of aldol addition, cyclization, rearrangement, and conjugate addition reactions, leading to the target products with moderate to good chemical yields and diastereoselectivity.
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Shanghai 201203, China.|School of Pharmacy, China Pharmaceutical University , Jiangsu, Nanjing 210009, China.
authors.forename: Tingting
authors.initials: T
authors.lastname: Li
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Shanghai 201203, China.
authors.forename: Shengbin
authors.initials: S
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Shanghai 201203, China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU , Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain.
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.affiliation: IKERBASQUE, Basque Foundation for Science , Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain.
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Shanghai 201203, China.|School of Pharmacy, China Pharmaceutical University , Jiangsu, Nanjing 210009, China.
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D034442:N-substituted Glycines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D034442:N-substituted Glycines