TY - JOUR
T1 - Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide
AU - Yang, Peng
AU - Lim, Li Hui
AU - Chuanprasit, Pratanphorn
AU - Hirao, Hajime
AU - Zhou, Jianrong(Steve)
PY - 2016/9/19
Y1 - 2016/9/19
N2 - An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one-pot synthesis of tetrahydroquinoxalines was also developed starting directly from α-ketoaldehydes and 1,2-diaminobenzene. Formic acid was used as a safe and economic surrogate for high-pressure hydrogen gas. Strongly σ-donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.
AB - An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one-pot synthesis of tetrahydroquinoxalines was also developed starting directly from α-ketoaldehydes and 1,2-diaminobenzene. Formic acid was used as a safe and economic surrogate for high-pressure hydrogen gas. Strongly σ-donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.
KW - chiral alkylamines
KW - nickel
KW - reductive amination
KW - synthetic methods
KW - transfer hydrogenation
UR - http://www.scopus.com/inward/record.url?scp=84992163252&partnerID=8YFLogxK
UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84992163252&origin=recordpage
U2 - 10.1002/anie.201606821
DO - 10.1002/anie.201606821
M3 - RGC 21 - Publication in refereed journal
SN - 1433-7851
VL - 55
SP - 12083
EP - 12087
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 39
ER -