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

[41] Enantioselective Amination of 4-Substituted Pyrazolones Catalyzed by Oxindole-Containing Thioureas and by a Recyclable Linear-Polymer-Supported Analogue in a Continuous Flow Process
Sanchez-Molpeceres, Rodrigo
Martin, Laura
Esteban, Noelia
Miguel, Jesus A.
Maestro, Alicia
Andres, Jose M.
JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 330 - 344
[42] Synthesis of chiral 4-substituted γ-lactams and corresponding γ-aminobutyric acids (Review)
Lebedev, A.
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (06): : 803 - 816
[43] Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine
Zai-Kun Xue
Nian-Kai Fu
San-Zhong Luo
Chinese Chemical Letters, 2017, 28 (05) : 1083 - 1086
[44] Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine
Xue, Zai-Kun
Fu, Nian-Kai
Luo, San-Zhong
CHINESE CHEMICAL LETTERS, 2017, 28 (05) : 1083 - 1086
[45] THE THERMAL-PROPERTIES OF (4-SUBSTITUTED CYCLOHEXYL) 4-SUBSTITUTED CINNAMATES
HAYASHI, S
TAKENAKA, S
KUSABAYASHI, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (01) : 283 - 284
[46] Palladium-Catalyzed Asymmetric Hydrogenation of 4-Substituted 3-Alkoxycarbonylfuran-2(5H)-ones
Gao, Xuan-Yu
Wang, Han
Jing, Huan
Yu, Chang-Bin
Zhou, Yong-Gui
JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (10): : 3752 - 3761
[47] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .4.
HEGEDUS, LS
SESTRICK, MR
MICHAELSON, ET
HARRINGTON, PJ
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17): : 4141 - 4146
[48] Diastereoselective Palladium-Catalyzed α-Arylation of 4-Substituted Cyclohexyl Esters
Bercot, Eric A.
Caille, Seb
Bostick, Tracy M.
Ranganathan, Krishnakumar
Jensen, Randy
Faul, Margaret M.
ORGANIC LETTERS, 2008, 10 (22) : 5251 - 5254
[49] Flexible, Phase-Transfer Catalyzed Approaches to 4-Substituted Prolines
Johnston, Heather J.
McWhinnie, Fergus S.
Landi, Felicetta
Hulme, Alison N.
ORGANIC LETTERS, 2014, 16 (18) : 4778 - 4781
[50] 4-SUBSTITUTED STEROIDS
ATWATER, NW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (11) : 2847 - 2852

← 1 2 3 4 5 →