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

[21] Biomimetic asymmetric transamination reactions catalyzed by axial pyroxamine organocatalysts: Mechanism and origin of stereoselectivity
Han, Li-Li
Xia, Ruihao
Zeng, Xitao
Li, Zhanwei
Qiao, Yan
Wei, Donghui
MOLECULAR CATALYSIS, 2023, 549
[22] ASYMMETRIC TRANSAMINATION FROM AMINO-ACIDS .2. ASYMMETRIC SYNTHESIS OF AMINES BY CHEMICAL TRANSAMINATION OF OPTICALLY-ACTIVE AMINO-ACIDS TO KETONES
YAMADA, SI
IKOTA, N
ACHIWA, K
TETRAHEDRON LETTERS, 1976, (13) : 1001 - 1004
[23] Zinc Catalyzed and Mediated Asymmetric Propargylation of Trifluoromethyl Ketones with a Propargyl Boronate
Fandrick, Daniel R.
Reeves, Jonathan T.
Bakonyi, Johanna M.
Nyalapatla, Prasanth R.
Tan, Zhulin
Niemeier, Oliver
Akalay, Deniz
Fandrick, Keith R.
Wohlleben, Wolfgang
Ollenberger, Swetlana
Song, Jinhua J.
Sun, Xiufeng
Qu, Bo
Haddad, Nizar
Sanyal, Sanjit
Shen, Sherry
Ma, Shengli
Byrne, Denis
Chitroda, Ashish
Fuchs, Victor
Narayanan, Bikshandarkoil A.
Grinberg, Nelu
Lee, Heewon
Yee, Nathan
Brenner, Michael
Senanayake, Chris H.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 3592 - 3615
[24] Organocatalytic Asymmetric Biomimetic Transamination: From α-Keto Esters to Optically Active α-Amino Acid Derivatives
Xiao, Xiao
Xie, Ying
Su, Cunxiang
Liu, Mao
Shi, Yin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12914 - 12917
[25] Ru-Catalyzed Asymmetric Reductive Amination of Aryl-Trifluoromethyl Ketones for Synthesis of Primary α-(Trifluoromethyl)arylmethylamines
Wang, Yuan-Zheng
Hu, Le'an
Bai, Shao-Tao
Zhang, Xumu
ORGANIC LETTERS, 2023, 25 (27) : 5033 - 5037
[26] Asymmetric aldol reactions of trifluoromethyl ketones with a chiral Ni(II) complex of glycine: Stereocontrolling effect of the trifluoromethyl group
Soloshonok, VA
Avilov, DV
Kukhar, VP
TETRAHEDRON, 1996, 52 (38) : 12433 - 12442
[27] A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones
Anthore, Lucile
Zard, Samir Z.
ORGANIC LETTERS, 2015, 17 (12) : 3058 - 3061
[28] One-pot asymmetric synthesis of α-trifluoromethylated amines from α-trifluoromethyl ketones
Xu, Jian
Liu, Zhen-Jiang
Yang, Xian-Jin
Wang, Li-Min
Chen, Guan-Long
Liu, Jin-Tao
TETRAHEDRON, 2010, 66 (46) : 8933 - 8937
[29] Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones
Crotti, Simone
Belletti, Giada
Di Iorio, Nicola
Marotta, Emanuela
Mazzanti, Andrea
Righi, Paolo
Bencivenni, Giorgio
RSC ADVANCES, 2018, 8 (58): : 33451 - 33458
[30] Asymmetric hydrogenation of trifluoromethyl ketones: application in the synthesis of Odanacatib and LX-1031
Zhu, Tiao-Zhen
Shao, Pan-Lin
Zhang, Xumu
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (14) : 3705 - 3711

← 1 2 3 4 5 →