Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions.
A nickel-catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious-metal catalysis.
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA. nick.desrosiers@boehringer-ingelheim.com.
Jean-Nicolas
0000-0003-3859-2390
JN
Desrosiers
Department of Chemistry and Biochemistry, University of California, Los Angeles, USA.
Liana
L
Hie
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Soumik
S
Biswas
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Olga V
OV
Zatolochnaya
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Sonia
S
Rodriguez
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Heewon
H
Lee
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Nelu
N
Grinberg
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Nizar
N
Haddad
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Nathan K
NK
Yee
Department of Chemistry and Biochemistry, University of California, Los Angeles, USA.
Neil K
NK
Garg
Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.
Chris H
CH
Senanayake
Heck reaction; cyclization; heterocycles; homogeneous catalysis; nickel