Asymmetric Synthesis of Trifluoromethylated Amines via Catalytic Enantioselective Isomerization of Imines

被引：120

作者：

Wu, Yongwei ^{[1
]}

Deng, Li ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 35期

基金：

美国国家卫生研究院;

关键词：

PHENYLETHANOLAMINE N-METHYLTRANSFERASE; ALPHA-KETO ESTERS; BIOMIMETIC TRANSAMINATION; BOND FORMATION; FLUORINE; QUATERNARY; ACIDS; HYDROGENATION; INHIBITORS; KETIMINES;

D O I：

10.1021/ja306771n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new approach toward the asymmetric synthesis of optically active trifluoromethylated amines was enabled by an unprecedented, highly enantioselective catalytic isomerization of trifluoromethyl imines with a new chiral organic catalyst. Not only aryl but also alkyl trifluoromethylated amines could be obtained in high enantioselectivities.

引用

页码：14334 / 14337

页数：4

共 50 条

[1] Unprecedented enantioselective reduction of N-unsubstituted imines: Catalytic asymmetric synthesis of trifluoromethylated amines.
Gosselin, F
O'Shea, PD
Roy, S
Reamer, R
Chen, CY
Volante, RP
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U555 - U555
[2] Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source
Wang, Zheting
Yang, Chunhui
Chen, Jingchao
Yang, Fan
Khan, Ruhima
Yang, Yong
Qiao, Xingfang
Su, Zhimin
Fan, Baomin
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1530 - 1535
[3] Asymmetric Synthesis of Trifluoromethylated Amines and Their Derivatives
Cheng, Gui-Lin
Wang, Hui
Lin, Xian-Fu
Wu, Qi
[J]. CURRENT ORGANIC SYNTHESIS, 2016, 13 (04) : 514 - 543
[4] Asymmetric, catalytic phenyl transfer to imines:: Highly enantioselective synthesis of diarylmethylamines
Hermanns, N
Dahmen, S
Bolm, C
Bräse, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (19) : 3692 - 3694
[5] Enantioselective synthesis of phospholenes via asymmetric organocatalytic alkene isomerization
Hintermann, Lukas
Schmitz, Marco
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) : 1469 - 1473
[6] ASYMMETRIC IMINE ISOMERIZATION IN THE ENANTIOSELECTIVE SYNTHESIS OF CHIRAL AMINES FROM PROCHIRAL KETONES
WILLEMS, JGH
DEVRIES, JG
NOLTE, RJM
ZWANENBURG, B
[J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3917 - 3920
[7] ASYMMETRIC REDUCTION OF PHOSPHINYL IMINES WITH HYDRIDE REAGENTS - ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PRIMARY AMINES
HUTCHINS, RO
ABDELMAGID, A
STERCHO, YP
WAMBSGANS, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04): : 702 - 704
[8] Catalytic enantioselective synthesis of macrolides via asymmetric alkylation
Jones, G. B.
Huber, R. S.
Chapman, B. J.
[J]. Tetrahedron: Asymmetry, 8 (11):
[9] Catalytic enantioselective synthesis of macrolides via asymmetric alkylation
Jones, GB
Huber, RS
Chapman, BJ
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (11) : 1797 - 1809
[10] Synthesis of ?,?-Chiral Trifluoromethylated Amines through the Stereospecific Isomerization of ?-Chiral Allylic Amines
Garcia-Vazquez, Victor
Martinez-Pardo, Pablo
Postole, Alexandru
Inge, A. Ken
Martin-Matute, Belen
[J]. ORGANIC LETTERS, 2022, 24 (21) : 3867 - 3871

← 1 2 3 4 5 →