Rh(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective Synthesis of Spirooxindole-Fused Thiaindans

被引：36

作者：

Xiao, Guolan ^{[1
]}

Chen, Tiantian ^{[1
]}

Ma, Chaoqun ^{[1
]}

Xing, Dong ^{[1
]}

Hu, Wenhao ^{[1
,2
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug Dr, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 15期

基金：

美国国家科学基金会;

关键词：

TYROSINE-PHOSPHATASE B; 3-COMPONENT REACTIONS; ASYMMETRIC-SYNTHESIS; P53-MDM2; INHIBITORS; AMMONIUM YLIDES; SELECTIVE INHIBITORS; CASCADE REACTIONS; DIAZO-COMPOUNDS; IMINO ESTERS; DIELS-ALDER;

D O I：

10.1021/acs.orglett.8b01833

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric strategy for the construction of chiral sulfur-containing spirooxindole-fused heterocycles was achieved via a rhodium(II)/chiral phosphoric acid-cocatalyzed reaction between 2-mercaptophenyl ketones and 3-diazooxindoles. With this method, a series of spirooxindole-thiaindan derivatives bearing two contiguous quaternary carbon stereogenic centers were obtained in high yields with high diastereoselectivities and high-to-excellent enantioselectivities.

引用

页码：4531 / 4535

页数：5

共 50 条

[1] Rhodium(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O-H Bond Insertion of α-Diazo Esters
Zhang, Yiliang
Yao, Yuan
He, Li
Liu, Yang
Shi, Lei
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (16) : 2754 - 2761
[2] Enantioselective Synthesis of α-Mercapto-β-amino Esters via Rh(II)/Chiral Phosphoric Acid-Cocatalyzed Three-Component Reaction of Diazo Compounds, Thiols, and Imines
Xiao, Guolan
Ma, Chaoqun
Xing, Dong
Hu, Wenhao
[J]. ORGANIC LETTERS, 2016, 18 (23) : 6086 - 6089
[3] Chiral sulfinamidourea and strong Bronsted acid-cocatalyzed enantioselective Povarov reaction to access tetrahydroquinolines
Xu, Hao
Zhang, Hu
Jacobsen, Eric N.
[J]. NATURE PROTOCOLS, 2014, 9 (08) : 1860 - 1866
[4] Dynamic Kinetic Stereoselective Glycosylation via RhII and Chiral Phosphoric Acid-Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates
Wu, Jicheng
Jia, Peijing
Kuniyil, Rositha
Liu, Peng
Tang, Weiping
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (39)
[5] Rh2(OAc)4 and Chiral Phosphoric Acid Cocatalyzed Highly Diastereo- and Enantioselective Four-Component Reactions: Facile Synthesis of Chiral α,β-Diamino Acid Derivatives
Jing, Changcheng
Xing, Dong
Qian, Yu
Hu, Wenhao
[J]. SYNTHESIS-STUTTGART, 2014, 46 (10): : 1348 - 1354
[6] Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking
Mori, Keiji
Miyake, Ayaka
Akiyama, Takahiko
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (89) : 16107 - 16110
[7] Chiral Sulfide/Phosphoric Acid Cocatalyzed Enantioselective Intermolecular Oxysulfenylation of Alkenes with Phenol and Alcohol O-Nucleophiles
Liu, Xiao-Dong
Luo, Yicong
Huo, Xiaohong
Luo, Hui-Yun
Cao, Ren-Fei
Chen, Zhi-Min
[J]. CCS CHEMISTRY, 2022, 4 (10): : 3342 - 3354
[8] Enantioselective synthesis of spirocycles through a chiral phosphoric acid catalyzed desymmetrization
Minerali, Eni
Kelley, Amber
Stingley, Kyla
Wilent, Jennifer
Chambers, Nicholas
Wilson, G. Tyler
Petersen, Kimberly
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[9] Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis
Wang, Lei
Rahman, Abdul
Lin, Xufeng
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (28) : 6033 - 6041
[10] Enantioselective Synthesis of Chiral Amides by a Phosphoric Acid Catalyzed Asymmetric Wolff Rearrangement
Pan, Jia-Bin
Yang, Zhi-Chun
Zhang, Xuan-Ge
Li, Mao-Lin
Zhou, Qi-Lin
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (39)

← 1 2 3 4 5 →