title: Highly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins.
abstract: The first asymmetric Michael addition of 3-substituted phthalides to nitroolefins promoted by amino acid-incorporating multifunctional catalysts has been developed. The reported method led to the synthesis of 3,3-disubstituted phthalide derivatives in high yields, and in a highly diastereoselective and enantioselective manner. Facile synthesis of a chiral bicyclic lactam has also been demonstrated.
authors.affiliation: Department of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
authors.forename: Jie
authors.initials: J
authors.lastname: Luo
authors.forename: Haifei
authors.initials: H
authors.lastname: Wang
authors.forename: Fangrui
authors.initials: F
authors.lastname: Zhong
authors.forename: Jacek
authors.initials: J
authors.lastname: Kwiatkowski
authors.forename: Li-Wen
authors.initials: LW
authors.lastname: Xu
authors.forename: Yixin
authors.initials: Y
authors.lastname: Lu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D001572:Benzofurans / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000596:Amino Acids; D001572:Benzofurans; D007769:Lactams; C082022:phthalide