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Synthesis 2023; 55(12): 1929-1939
DOI: 10.1055/a-2017-4738
paper
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Enantioselective Synthesis of Dispirooxindole Derivatives via Asymmetric Catalytic Cascade Reactions

Rui Ma
a   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000, P. R. of China
,
Jia-Lu Zhang
a   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000, P. R. of China
,
Xiu-Qin Hu∗
a   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000, P. R. of China
,
Peng-Fei Xu∗
a   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000, P. R. of China
b   State Key Laboratory of Veterinary Etiological Biology, College of Veterinary Medicine, Lanzhou University, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou, P. R. of China
c   Frontiers Science Center for Rare Isotopes, Lanzhou University, Lanzhou, P. R. of China
› Author AffiliationsWe are grateful to the National Natural Science Foundation of China (NSFC) (21632003, 21871116, 22071085), the Key Program of Gansu Province (17ZD2GC011), and the ‘111’ Program from the MOE of P. R. China for funding the research.
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Dedicated to Prof. Guo-Qiang Lin for his 80th birthday.

Abstract

A series of optically active 3,3′-pyrrolidinyl-dispirooxindole derivatives containing a CF3 moiety have been efficiently constructed through asymmetric catalytic cascade reactions catalyzed by cinchona-derived bifunctional squaramide catalyst, bearing four contiguous stereogenic centers, two of which are vicinal spiro-stereocenters. Additionally, a wide range of substituted products were achieved with moderate to high yields (up to 99% yield) and excellent stereoselectivities (up to >20:1 dr for all cases and up to 99% ee).

Key words

organocatalysis - dispirooxindole - cascade reactions - four contiguous stereogenic centers - new substrates

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2017-4738.
  • Supporting Information


Publication History

Received: 16 December 2022

Accepted after revision: 22 January 2023

Accepted Manuscript online:
22 January 2023

Article published online:
27 February 2023

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