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Cu-Catalyzed Direct Enantioselective Vinylogous Mannich Reaction between ß,γ-Unsaturated Pyrazoleamides and Ketimines.
Luo, Ling-Shan; Hou, Si-Meng; Lu, Jian; Zhang, Qi; Sha, Feng; Wu, Xin-Yan.
Affiliation
  • Luo LS; Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
  • Hou SM; Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
  • Lu J; Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
  • Zhang Q; Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
  • Sha F; Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
  • Wu XY; Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
J Org Chem ; 89(4): 2582-2587, 2024 Feb 16.
Article in En | MEDLINE | ID: mdl-38284164
ABSTRACT
A catalytic asymmetric vinylogous Mannich-type reaction between ß,γ-unsaturated amides and ketimines has been developed in excellent regio-, diastereo-, and enantioselectivities. The methodology provides an efficient approach to construct chiral homoallylic amines with a 3-amino-2-oxindole scaffold. Moreover, the transformations of the chiral products, including the removal of the pyrazole group or Boc group, the reduction of the C-C double bond, and Suzuki coupling, have been investigated.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2024 Document type: Article Country of publication:
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2024 Document type: Article Country of publication: