A one- pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination ( ARA)

Yang, Tao1; Yin, Qin1; Gu, Guoxian1; Zhang, Xumu1,2

2018-07-04

10.1039/c8cc03586e

CHEMICAL COMMUNICATIONS   影响因子和分区

1359-7345

1364-548X

Asymmetric reductive amination for the synthesis of both chiral tetrahydroquinolines (THQs) and tetrahydroisoquinolines (THIQs) has been realized with an Ir/ZhaoPhos catalytic system via a one-pot N-Boc deprotection/intramolecular asymmetric reductive amination (ARA) sequence. Control experiments reveal that HCl plays a vital role to the success of this transformation. The HCl acid assists the removal of the N-Boc protecting group and also provides chloride ions to interact with the thiourea moiety in ZhaoPhos, thus leading to excellent reaction enantiocontrol.

SCI ; EI ; IC ; CCR

英语

NI期刊 ; NI论文

第一 ; 通讯

Shenzhen Science and Technology Innovation Committee[JCYJ20170817110055425] ; Shenzhen Science and Technology Innovation Committee[JCYJ20170817104853520]

Chemistry

Chemistry, Multidisciplinary

WOS:000436290100033

ROYAL SOC CHEMISTRY

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
2.Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China

Yang, Tao,Yin, Qin,Gu, Guoxian,et al. A one- pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination ( ARA)[J]. CHEMICAL COMMUNICATIONS,2018,54(52):7247-7250.

Yang, Tao,Yin, Qin,Gu, Guoxian,&Zhang, Xumu.(2018).A one- pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination ( ARA).CHEMICAL COMMUNICATIONS,54(52),7247-7250.

Yang, Tao,et al."A one- pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination ( ARA)".CHEMICAL COMMUNICATIONS 54.52(2018):7247-7250.