title: Organocatalytic and electrophilic approach to oxindoles with C3-quaternary stereocenters.
abstract: A Lewis base-catalyzed asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates derived from isatins has been investigated, which provides an electrophilic pathway to access oxindoles bearing C3-quaternary stereocenters. Excellent diastereoselectivity and high enantioselectivity have been obtained in the vinylogous functionalization of α,α-dicyanoolefin nucleophiles, giving multifunctional products with vicinal quaternary and tertiary chiral carbon centers.
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Peng
authors.forename: Xin
authors.initials: X
authors.lastname: Huang
authors.forename: Hai-Lei
authors.initials: HL
authors.lastname: Cui
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000478:Alkylation; D002384:Catalysis; D018360:Crystallography, X-Ray; D004583:Electrons; D007211:Indoles / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D058115:Lewis Bases; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole