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Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines.
Zhao, Lei; Meng, Xiao; Zou, Yifeng; Zhao, Junsong; Wang, Lili; Zhang, Lanlan; Wang, Chao.
Affiliation
  • Zhao L; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Meng X; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Zou Y; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Zhao J; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Wang L; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Zhang L; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Wang C; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
Org Lett ; 23(21): 8516-8521, 2021 Nov 05.
Article in En | MEDLINE | ID: mdl-34633190
ABSTRACT
We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or ß-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.

Full text: 1 Collection: 01-internacional Database: MEDLINE Type of study: Guideline Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2021 Document type: Article

Full text: 1 Collection: 01-internacional Database: MEDLINE Type of study: Guideline Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2021 Document type: Article