Organocatalytic enantio- and diastereoselective synthesis of trifluoro-ethylamine allenoate derivatives containing axial and central chiralities

被引：3

作者：

Shi, Siyu ^{[1
]}

Gu, Mengyun ^{[1
]}

Chen, Danna ^{[4
]}

Li, Ruya ^{[2
]}

Shen, Zhiqiang ^{[1
,3
]}

Huang, Jinqi ^{[4
]}

Yan, Wenjin ^{[1
]}

机构：

[1] Lanzhou Univ, Inst Pharmacol, Sch Basic Med Sci, Lanzhou 730000, Peoples R China

[2] Guangdong Med Univ, Affiliated Hosp, Zhanjiang, Guangdong, Peoples R China

[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Gansu, Peoples R China

[4] Guangzhou Med Univ, Guangzhou Peoples Hosp 1, Inst Blood Transfus & Hematol, Dept Hematol, Guangzhou, Guangdong, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 79期

基金：

中国国家自然科学基金;

关键词：

BETA; GAMMA-ALKYNYL-ALPHA-IMINO ESTERS; FLUORINE; FENPROSTALENE;

D O I：

10.1039/d4cc03297g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report an example of a stereoselectivec-addition reac-tion of trifluoromethyl ketimines to 1-alkynyl ketones mediatedby an isothiourea, BTM, under mild conditions, which affordedtetrasubstituted allenes with central chiralities in high yields (upto 94% yield), good enantioselectivities (up to 91% ee), and excellentdiastereoselectivities (all420 : 1 dr). In addition, the BTM-catalyzedc-addition reaction was successfully applied to the gram-scale reac-tion, and an unexpected benzopyrrolothiazine derivative was success-fully converted, albeit racemic.

引用

页码：11116 / 11119

页数：4

共 41 条

[1] Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination [J].

Baig, He-Yuan ;

Tan, Fu-Xin ;

Liu, Tuan-Qing ;

Zhu, Guo-Dong ;

Tian, Jin-Miao ;

Ding, Tong-Mei ;

Chen, Zhi-Min ;

Zhang, Shu-Yu .

NATURE COMMUNICATIONS, 2019, 10 (1)

[2] Enantioselective Synthesis of Atropisomers with Multiple Stereogenic Axes [J].

Bao, Xiaoze ;

Rodriguez, Jean ;

Bonne, Damien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) :12623-12634

[3] Benzotetramisole: A remarkably enantioselective acyl transfer catalyst [J].

Birman, VB ;

Li, XM .

ORGANIC LETTERS, 2006, 8 (07) :1351-1354

[4] Chiral Allene-Containing Phosphines in Asymmetric Catalysis [J].

Cai, Feng ;

Pu, Xiaotao ;

Qi, Xiangbing ;

Lynch, Vincent ;

Radha, Akella ;

Ready, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) :18066-18069

[5] SYNTHESIS AND GASTRIC ANTISECRETORY PROPERTIES OF ALLENIC 16-PHENOXY-OMEGA-TETRANOR PROSTAGLANDIN-E ANALOGS [J].

CARPIO, H ;

COOPER, GF ;

EDWARDS, JA ;

FRIED, JH ;

GARAY, GL ;

GUZMAN, A ;

MENDEZ, JA ;

MUCHOWSKI, JM ;

ROSZKOWSKI, AP ;

VANHORN, AR ;

WREN, D .

PROSTAGLANDINS, 1987, 33 (02) :169-180

[6] Organocatalytic Asymmetric Synthesis of α-Trifluoromethyl Homoallylic Amine Derivatives from Trifluoromethyl-Containing Ketoimines and Isatin-Derived Morita-Baylis-Hillman Carbonates [J].

Chen, Danna ;

Deng, Yabo ;

Sun, Shuo ;

Jia, Pengfei ;

Huang, Jinqi ;

Yan, Wenjin .

ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (02) :178-193

[7] Applications of Fluorine in Medicinal Chemistry [J].

Gillis, Eric P. ;

Eastman, Kyle J. ;

Hill, Matthew D. ;

Donnelly, David J. ;

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (21) :8315-8359

[8] A new sesquiterpenoid with cytotoxic and anti-inflammatory activity from the leaves of Datura metel L [J].

Guo, Rui ;

Liu, Yan ;

Pan, Juan ;

Guan, Wei ;

Yang, Bing-You ;

Kuang, Hai-Xue .

NATURAL PRODUCT RESEARCH, 2021, 35 (04) :607-613

[9] The many roles for fluorine in medicinal chemistry [J].

Hagmann, William K. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369

[10] C-Selective and Diastereoselective Alkyl Addition to β,γ-Alkynyl-α-imino Esters with Zinc(II)ate Complexes [J].

Hatano, Manabu ;

Yamashita, Kenji ;

Mizuno, Mai ;

Ito, Orie ;

Ishihara, Kazuaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (09) :2707-2711

← 1 2 3 4 5 →