title: Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: use of prochiral nucleophiles.
abstract: The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds.
authors: Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore 3, Science Drive 3, Singapore 117543 (Singapore).
authors: Tianli
authors: T
authors: Wang
authors: Weijun
authors: W
authors: Yao
authors: Fangrui
authors: F
authors: Zhong
authors: Guo Hao
authors: GH
authors: Pang
authors: Yixin
authors: Y
authors: Lu
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry; D000078183:Oxindoles; D010720:Phosphines / Q000737:chemistry*; D010830:Physostigmine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D001688:Biological Products; D005231:Fatty Acids, Unsaturated; D007211:Indoles; D000078183:Oxindoles; D010720:Phosphines; C518152:esermethole; C022960:2-oxindole; D007495:Iridium; C035369:2-butynoic acid; D010830:Physostigmine; C044646:phosphine
keywords: allylation; bifunctional phosphines; oxindoles; quaternary carbon centers; γ-addition