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Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction.
Li, Xiang; Zhou, Bo; Yang, Run-Ze; Yang, Fu-Ming; Liang, Ren-Xiao; Liu, Ren-Rong; Jia, Yi-Xia.
Afiliación
  • Li X; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
  • Zhou B; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
  • Yang RZ; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
  • Yang FM; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
  • Liang RX; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
  • Liu RR; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
  • Jia YX; College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology , Zhejiang University of Technology , Chaowang Road 18# , Hangzhou 310014 , China.
J Am Chem Soc ; 140(42): 13945-13951, 2018 10 24.
Article en En | MEDLINE | ID: mdl-30256629
Enantioselective intramolecular dearomative Heck reactions have been developed by Pd-catalyzed cross-coupling of aryl halides or aryl triflates with the internal C═C bond of indoles, benzofurans, pyrroles, and furans. A variety of structurally unique spiroheterocycles and benzofused heterocycles having N/O-substituted quaternary carbon stereocenters, and exocyclic olefin moieties were afforded in moderate to excellent yields with good to excellent enantioselectivities, showing a broad scope of the present protocol. A series of new BINOL- and H8-BINOL-based phosphoramidite ligands were synthesized and proved to be efficient chiral ligands in the reactions of C2-tethered substrates to form spiroheterocycles. ( S)-SEGPHOS turned out to be a good ligand for the reaction delivering benzofused indolines and pyrrolines. Synthetic applications based on transformations of the exocyclic double bonds were realized without loss of enantiopurities, including hydrogenation, hydroborylation, and stereospecific ring-expanding rearrangement.

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2018 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2018 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos