Iridium-catalyzed asymmetric hydrogenation of 3-substituted unsaturated oxindoles to prepare C3-mono substituted oxindoles

被引：29

作者：

Liu, Yuanyuan ^{[1
]}

Yao, Dongmei ^{[1
]}

Li, Kun ^{[1
]}

Tian, Fengtao ^{[1
]}

Xie, Fang ^{[1
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 44期

关键词：

Asymmetric hydrogenation; Iridium complex; Tropos phosphine-oxazoline ligands; 3-Substituted unsaturated oxindoles; Chiral C3-mono substituted oxindoles; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; STEREOSELECTIVE-SYNTHESIS; OXAZOLINE LIGANDS; CONCISE SYNTHESIS; MANNICH REACTION; REARRANGEMENT; COMPLEXES; ALKALOIDS; DERIVATIVES;

D O I：

10.1016/j.tet.2011.09.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and enantioselective hydrogenation of 3-substituted unsaturated oxindoles has been developed by an iridium complex of tropos phosphine-oxazoline ligands. It is the first example to prepare chiral C3-mono substituted oxindoles via asymmetric catalysis. And the reaction provides instant access to this kind of compounds with excellent conversion and enantioselectivities (up to 93% ee). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：8445 / 8450

页数：6

共 50 条

[31] Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
Yang, Xiao-Hui
Yue, Hai-Tao
Yu, Na
Li, Yi-Pan
Xie, Jian-Hua
Zhou, Qi-Lin
CHEMICAL SCIENCE, 2017, 8 (03) : 1811 - 1814
[32] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized, Trialkyl-Substituted Olefins
Wang, Aie
Fraga, Rui P. A.
Hoermann, Esther
Pfaltz, Andreas
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) : 599 - 606
[33] Chiral N,N′-Dioxide/Scandium(III)-Catalyzed Asymmetric Alkylation of N-Unprotected 3-Substituted Oxindoles
He, Changqiang
Cao, Weidi
Zhang, Jianlin
Ge, Shulin
Feng, Xiaoming
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (22) : 4301 - 4305
[34] Chiral Iminophosphorane Organocatalyzed Asymmetric Sulfenylation of 3-Substituted Oxindoles: Substrate-Interrelated Enantioselectivities
Gao, Xing
Han, Jianwei
Wang, Limin
SYNTHESIS-STUTTGART, 2016, 48 (16): : 2603 - 2611
[35] Synthesis of 3-substituted 3-fluoro-2-oxindoles by deacylative alkylation
Molina, Cynthia
Ortega-Martinez, Aitor
Sansano, Jose M.
Najera, Carmen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) : 482 - 489
[36] Enantioselective synthesis of 3-substituted dihydrobenzofurans through iridium-catalyzed intramolecular hydroarylation
Sakamoto, Kana
Nishimura, Takahiro
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (03) : 684 - 690
[37] Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
Yu, Jin-Sheng
Zhou, Feng
Liu, Yun-Lin
Zhou, Jian
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1360 - 1365
[38] Chiral Calcium VAPOL Phosphate Mediated Asymmetric Chlorination and Michael Reactions of 3-Substituted Oxindoles
Zheng, Wenhua
Zhang, Zuhui
Kaplan, Matthew J.
Antilla, Jon C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) : 3339 - 3341
[39] Squaramide-catalyzed diastereo- and enantioselective Michael addition of 3-substituted oxindoles to nitroalkenes
Yang, Wen
Wang, Jingsi
Du, Da-Ming
TETRAHEDRON-ASYMMETRY, 2012, 23 (13) : 972 - 980
[40] A highly efficient thiourea catalyzed dehydrative nucleophilic substitution reaction of 3-substituted oxindoles with xanthydrols
Chen, Long
Zhu, Feng
Wang, Cui-Hong
Zhou, Jian
RSC ADVANCES, 2013, 3 (43): : 19880 - 19884

← 1 2 3 4 5 →