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Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins with Vinyl Sulfones.
J Org Chem. 2023 Mar 17; 88(6):3802-3807.JO

Abstract

The organocatalytic asymmetric Morita-Baylis-Hillman (MBH) reaction of isatin derivatives with various vinyl sulfones is disclosed. Chiral sulfone-containing 3-hydroxyoxindoles were produced in good to high yields and with good to high ee's. This report displays an unprecedented example to apply activated alkenes with sulfone moiety other than carbonyl groups in asymmetric MBH reactions and provides an efficient strategy to incorporate the sulfone functional group for the synthesis of chiral 3-hydroxyoxindoles.

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Authors+Show Affiliations

He HJ
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Wang RQ
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Wan LX
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Zhou LY
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Li HY
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Li GB
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Xiao YC
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Chen FE
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China. Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

36822154

Citation

He, Hong-Jiao, et al. "Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins With Vinyl Sulfones." The Journal of Organic Chemistry, vol. 88, no. 6, 2023, pp. 3802-3807.
He HJ, Wang RQ, Wan LX, et al. Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins with Vinyl Sulfones. J Org Chem. 2023;88(6):3802-3807.
He, H. J., Wang, R. Q., Wan, L. X., Zhou, L. Y., Li, H. Y., Li, G. B., Xiao, Y. C., & Chen, F. E. (2023). Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins with Vinyl Sulfones. The Journal of Organic Chemistry, 88(6), 3802-3807. https://doi.org/10.1021/acs.joc.2c03073
He HJ, et al. Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins With Vinyl Sulfones. J Org Chem. 2023 Mar 17;88(6):3802-3807. PubMed PMID: 36822154.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins with Vinyl Sulfones. AU - He,Hong-Jiao, AU - Wang,Rui-Qi, AU - Wan,Lin-Xi, AU - Zhou,Li-Yan, AU - Li,Hong-Yan, AU - Li,Guo-Bo, AU - Xiao,You-Cai, AU - Chen,Fen-Er, Y1 - 2023/02/23/ PY - 2023/2/24/pubmed PY - 2023/2/24/medline PY - 2023/2/23/entrez SP - 3802 EP - 3807 JF - The Journal of organic chemistry JO - J Org Chem VL - 88 IS - 6 N2 - The organocatalytic asymmetric Morita-Baylis-Hillman (MBH) reaction of isatin derivatives with various vinyl sulfones is disclosed. Chiral sulfone-containing 3-hydroxyoxindoles were produced in good to high yields and with good to high ee's. This report displays an unprecedented example to apply activated alkenes with sulfone moiety other than carbonyl groups in asymmetric MBH reactions and provides an efficient strategy to incorporate the sulfone functional group for the synthesis of chiral 3-hydroxyoxindoles. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/36822154/Organocatalytic_Asymmetric_Morita_Baylis_Hillman_Reaction_of_Isatins_with_Vinyl_Sulfones_ DB - PRIME DP - Unbound Medicine ER -