Chiral iminophosphorane catalyzed asymmetric sulfenylation of 4-substituted pyrazolones

被引：28

作者：

Han, Jianwei ^{[1
,2
]}

Zhang, Yanxia ^{[1
,2
]}

Wu, Xin-Yan ^{[1
]}

Wong, Henry N. C. ^{[2
]}

机构：

[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 03期

基金：

中国国家自然科学基金;

关键词：

MICHAEL ADDITION; STEREOCONTROLLED CONSTRUCTION; ENANTIOSELECTIVITY; PYRAZOL-5-ONES; TEMPERATURE; ALKYLATION; QUATERNARY; PYRAZOLIN-5-ONES; PALLADIUM; KETONES;

D O I：

10.1039/c8cc09049a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An excellent level of enantioselectivity in asymmetric sulfenylation of 4-substituted pyrazolones was achieved with chiral iminophosphorane as the organocatalyst under continuum solvation conditions (up to 99% ee). Importantly, this catalytic process features high efficiency with excellent enantioselectivities, easy separation of products, low catalytic loadings and scale-up to grams without loss of enantioselectivity.

引用

页码：397 / 400

页数：4

共 50 条

[21] ASYMMETRIC-SYNTHESIS WITH CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED AZETIDINONES
BALDWIN, SW
AUBE, J
TETRAHEDRON LETTERS, 1987, 28 (02) : 179 - 182
[22] ASYMMETRIC SULFENYLATION OF KETONES WITH CHIRAL SULFENAMIDES
HIROI, K
NISHIDA, M
NAKAYAMA, A
NAKAZAWA, K
FUJII, E
SATO, S
CHEMISTRY LETTERS, 1979, (08) : 969 - 972
[23] Organocatalytic Asymmetric Fluorination of 4-Substituted Isoxazolinones
Zhang, Huanrui
Wang, Baomin
Cui, Longchen
Bao, Xiaoze
Qu, Jingping
Song, Yuming
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (10) : 2143 - 2147
[24] Iodine-catalyzed sulfenylation of pyrazolones using dimethyl sulfoxide as an oxidant
Siddaraju, Yogesh
Prabhu, Kandikere Ramaiah
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (24) : 5191 - 5196
[25] Fast, highly enantioselective, and sustainable fluorination of 4-substituted pyrazolones catalyzed by amide-based phase-transfer catalysts
Wang, Yakun
Wang, Shuaifei
Wu, Yufeng
Zhao, Ting
Liu, Jie
Zheng, Junlin
Wang, Lin
Lv, Jieli
Zhang, Tao
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (09) : 2226 - 2233
[26] An approach to catalytic asymmetric deprotonation of 4-substituted cyclohexanones
Tetrahedron Lett, 45 (8195):
[27] Asymmetric Synthesis of Chiral α-Substituted Mercaptoglycine Derivatives via α-Sulfenylation of Ni(II) Complex of Glycine and S-Substituted 4-Methylbenzenesulfonothioate
Li, Jia
Song, Xiaohan
Zhou, Shengbin
Wang, Jiang
Liu, Hong
CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (09) : 1383 - 1390
[28] An approach to catalytic asymmetric deprotonation of 4-substituted cyclohexanones
Yamashita, T
Sato, D
Kiyoto, T
Kumar, A
Koga, K
TETRAHEDRON LETTERS, 1996, 37 (45) : 8195 - 8198
[29] Tartrate-derived iminophosphorane catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles with paraformaldehyde
Gao, Xing
Han, Jianwei
Wang, Limin
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (06): : 656 - 660
[30] PRACTICAL PREPARATION OF CHIRAL 4-SUBSTITUTED 2-OXAZOLIDINONES
ISHIZUKA, T
KIMURA, K
ISHIBUCHI, S
KUNIEDA, T
CHEMISTRY LETTERS, 1992, (06) : 991 - 994

← 1 2 3 4 5 →