Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles

Lu，Zhongyue1; Jia，Yanwen1; Chen，Xuling1; Li，Pengfei1,2

2022-03-04

10.1021/acs.joc.1c02917

JOURNAL OF ORGANIC CHEMISTRY   影响因子和分区

0022-3263

1520-6904

A type of Morita-Baylis-Hillman (MBH) carbonates has been developed from ninhydrin. These MBH carbonates have been successfully employed as 3C-synthons in the organocatalytic asymmetric [3 + 2]-annulations of the isatin-derived electron-deficient olefins, affording structurally diverse spirooxindoles in high yield with excellent stereoselectivity. In particular, the regioselectivity of MBH carbonates was controlled by the reaction partner, 3-methyleneoxindoles with carbonyl groups (R = ArCO), affording β-selective products and 3-methyleneoxindoles with ester groups (R = COMe) furnishing γ-selective products. The representative scale-up reactions and transformation of product were examined. The reaction mechanism was expounded by control experiments.

SCI ; EI

英语

第一 ; 通讯

National Natural Science Foundation of China[21871128] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province (South China University of Technology)[2018kf01]

Chemistry

Chemistry, Organic

WOS:000773458100092

AMER CHEMICAL SOC

20220811689922

Inorganic Compounds:804.2

CHEMISTRY

2-s2.0-85124896758

Scopus

1.Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,College of Science,Southern University of Science and Technology,Shenzhen,518055,China
2.Key Lab of Functional Molecular Engineering of Guangdong Province,South China University of Technology,Guangzhou,510006,China

Lu，Zhongyue,Jia，Yanwen,Chen，Xuling,et al. Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles[J]. JOURNAL OF ORGANIC CHEMISTRY,2022,87(5):3184-3194.

Lu，Zhongyue,Jia，Yanwen,Chen，Xuling,&Li，Pengfei.(2022).Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles.JOURNAL OF ORGANIC CHEMISTRY,87(5),3184-3194.

Lu，Zhongyue,et al."Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles".JOURNAL OF ORGANIC CHEMISTRY 87.5(2022):3184-3194.