title: Efficient Catalytic Kinetic Resolution of Spiro-epoxyoxindoles with Concomitant Asymmetric Friedel-Crafts Alkylation of Indoles.
abstract: An efficient process involving the catalytic kinetic resolution of racemic spiro-epoxyoxindoles with the simultaneous enantioselective Friedel-Crafts alkylation of indoles has been realized using a chiral phosphoric acid catalyst. The reaction provides two useful intermediates in high yields and excellent enantioselectivities. Performing the catalysis on a gram scale led to (R)-3-(3-indolyl)-oxindole-3-methanol, which was used in the asymmetric formal total synthesis of (+)-gliocladin C. Notably, the enantiomers (S)-3-(3-indolyl)-oxindole-3-methanol can be obtained easily by the reaction of the resolved spiro-epoxyoxindole with indole.
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.|Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Gongming
authors.initials: G
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Guangjun
authors.initials: G
authors.lastname: Bao
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Yiping
authors.initials: Y
authors.lastname: Li
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Wangsheng
authors.identifier: 0000-0001-5277-3329
authors.initials: W
authors.lastname: Sun
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.|Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.
authors.forename: Liang
authors.identifier: 0000-0002-3489-0633
authors.initials: L
authors.lastname: Hong
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Rui
authors.identifier: 0000-0002-4719-9921
authors.initials: R
authors.lastname: Wang
keywords: alkylation; asymmetric catalysis; kinetic resolution; organocatalysis; spiro-compounds