Asymmetric Biomimetic Transamination of Trifluoromethyl Ketones

被引：4

作者：

Cai, Weiqi ^{[1
,2
]}

Cai, Dongchen ^{[1
,2
]}

Liang, Hanyu ^{[1
,2
]}

Ren, Xinyi ^{[1
,2
]}

Zhao, Baoguo ^{[1
,2
]}

机构：

[1] Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Key Lab Resource Chem, Educ Minist, Shanghai 200234, Peoples R China

[2] Shanghai Normal Univ, Shanghai Frontiers Sci Ctr Biomimet Catalysis, Shanghai 200234, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 12期

基金：

中国国家自然科学基金;

关键词：

PHENYLETHANOLAMINE N-METHYLTRANSFERASE; AMINO-ACIDS; ENANTIOSELECTIVE ISOMERIZATION; CHIRAL-PYRIDOXAMINES; TRANSFER CATALYSIS; MECHANISM; AMINOTRANSFERASE; INHIBITORS; ESTERS;

D O I：

10.1021/acs.joc.2c02329

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of chiral pyridoxamine 4b as the catalyst and 2,2-diphenylglycine (3) as the amine source, asymmetric biomimetic transamination of trifluoromethyl ketones produces optically active alpha-trifluoromethyl amines 6 in 81-98% yields with 88-95% ee's under mild conditions.

引用

页码：7849 / 7857

页数：9

共 50 条

[1] An efficient synthesis of optically active trifluoromethyl aldimines via asymmetric biomimetic transamination
Liu, Mao
Li, Jing
Xiao, Xiao
Xie, Ying
Shi, Yian
CHEMICAL COMMUNICATIONS, 2013, 49 (14) : 1404 - 1406
[2] Efficient Asymmetric Biomimetic Aldol Reaction of Glycinates and Trifluoromethyl Ketones by Carbonyl Catalysis
Cheng, Aolin
Zhang, Liangliang
Zhou, Qinghai
Liu, Tao
Cao, Jing
Zhao, Guoqing
Zhang, Kun
Song, Guanshui
Zhao, Baoguo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (37) : 20166 - 20172
[3] Continuous-flow asymmetric biomimetic transamination
Soloshonok, Vadim A.
Catt, Hector T.
Ono, Taizo
JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (05) : 512 - 515
[4] Progress in asymmetric biomimetic transamination of carbonyl compounds
Xie, Ying
Pan, Hongjie
Liu, Mao
Xiao, Xiao
Shi, Yian
CHEMICAL SOCIETY REVIEWS, 2015, 44 (07) : 1740 - 1748
[5] Asymmetric biomimetic transamination of α-keto amides to peptides
Weiqi Cai
Xuelong Qiao
Hao Zhang
Bo Li
Jianhua Guo
Liangliang Zhang
Wen-Wen Chen
Baoguo Zhao
Nature Communications, 12
[6] Asymmetric biomimetic transamination of α-keto amides to peptides
Cai, Weiqi
Qiao, Xuelong
Zhang, Hao
Li, Bo
Guo, Jianhua
Zhang, Liangliang
Chen, Wen-Wen
Zhao, Baoguo
NATURE COMMUNICATIONS, 2021, 12 (01)
[7] Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination
Kang, Qi-Kai
Selvakumar, Sermadurai
Maruoka, Keiji
ORGANIC LETTERS, 2019, 21 (07) : 2294 - 2297
[8] ASYMMETRIC REDUCTION OF TRIFLUOROMETHYL KETONES WITH FERMENTING YEAST
BUCCIARELLI, M
FORNI, A
MELLI, M
MORETTI, I
TORRE, G
CHIMICA & L INDUSTRIA, 1980, 62 (02): : 168 - 169
[9] Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
Xie, Ying
Pan, Hongjie
Xiao, Xiao
Li, Songlei
Shi, Yian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (45) : 8960 - 8962
[10] Organocatalytic asymmetric biomimetic transamination of α-keto acetals to chiral α-amino acetals
Pan, Hongjie
Xie, Ying
Liu, Mao
Shi, Yian
RSC ADVANCES, 2014, 4 (05) : 2389 - 2392

← 1 2 3 4 5 →