4.7 Article

Enantioselective assembly of 3,3-disubstituted succinimides via three-component reaction of vinyl diazosuccinimides with alcohols and imines

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 65, Pages 8043-8046

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc02876f

Keywords

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Funding

  1. National Natural Science Foundation of China [21971262, 92056201]
  2. Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery [2019B030301005]
  3. Fundamental Research Funds for the Central Universities
  4. Sun Yat-sen University [2021 qntd44]
  5. Program for Guangdong Introducing Innovative and Entrepreneurial Teams [2016ZT06Y337]

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A cooperative catalysis of Rh-2(OAc)(4) and a chiral phosphoric acid has enabled an enantioselective three-component reaction to produce chiral 3,3-disubstituted succinimides with good to high yields and high to excellent enantioselectivity. The resulting product containing an alkenyl species can be easily converted to a chiral tricyclic structure under mild conditions.
An enantioselective three-component reaction of vinyl diazosuccinimdes with alcohols and imines has been realized by a cooperative catalysis of Rh-2(OAc)(4) and a chiral phosphoric acid, leading to chiral 3,3-disubstituted succinimides in good to high yields with high to excellent enantioselectivity. The generated product with an alkenyl species could be converted to the chiral tricyclic structure under mild conditions.

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