Tags

Type your tag names separated by a space and hit enter

Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles.
J Org Chem. 2022 03 04; 87(5):3184-3194.JO

Abstract

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 = CO2Me) furnishing γ-selective products. The representative scale-up reactions and transformation of product were examined. The reaction mechanism was expounded by control experiments.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Lu Z
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.
Jia Y
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.
Chen X
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.
Li P
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. Key Lab of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510006, China.

MeSH

CarbonatesCatalysisIsatinNinhydrinStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

35133821

Citation

Lu, Zhongyue, et al. "Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates With 3-Methyleneoxindoles." The Journal of Organic Chemistry, vol. 87, no. 5, 2022, pp. 3184-3194.
Lu Z, Jia Y, Chen X, et al. Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles. J Org Chem. 2022;87(5):3184-3194.
Lu, Z., Jia, Y., Chen, X., & Li, P. (2022). Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles. The Journal of Organic Chemistry, 87(5), 3184-3194. https://doi.org/10.1021/acs.joc.1c02917
Lu Z, et al. Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates With 3-Methyleneoxindoles. J Org Chem. 2022 03 4;87(5):3184-3194. PubMed PMID: 35133821.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita-Baylis-Hillman Carbonates with 3-Methyleneoxindoles. AU - Lu,Zhongyue, AU - Jia,Yanwen, AU - Chen,Xuling, AU - Li,Pengfei, Y1 - 2022/02/08/ PY - 2022/2/9/pubmed PY - 2022/4/19/medline PY - 2022/2/8/entrez SP - 3184 EP - 3194 JF - The Journal of organic chemistry JO - J Org Chem VL - 87 IS - 5 N2 - 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 = CO2Me) furnishing γ-selective products. The representative scale-up reactions and transformation of product were examined. The reaction mechanism was expounded by control experiments. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/35133821/Organocatalytic_Regio__and_Enantioselective_[3_+_2]_Annulations_of_Ninhydrin_Derived_Morita_Baylis_Hillman_Carbonates_with_3_Methyleneoxindoles_ DB - PRIME DP - Unbound Medicine ER -