Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis

被引：45

作者：

Zhu, Yugen ^{[1
]}

He, Wei ^{[1
]}

Wang, Wei ^{[1
]}

Pitsch, Chloe E. ^{[2
]}

Wang, Xiaotai ^{[2
]}

Wang, Xiang ^{[1
]}

机构：

[1] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA

[2] Univ Colorado, Dept Chem, Campus Box 194, Denver, CO 80217 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 40期

关键词：

asymmetric catalysis; cyclization; density functional calculations; polycycles; silver; CHIRAL SILVER PHOSPHATE; RESISTANT STAPHYLOCOCCUS-AUREUS; HOMOGENEOUS GOLD CATALYSIS; METAL CATALYSIS; TRICYCLIC INDOLINE; MODIFYING AGENT; BRONSTED ACID; COMPLEXES; LIGANDS; REARRANGEMENT;

D O I：

10.1002/anie.201706694

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported is the enantioselective synthesis of tetracyclic indolines using silver(I)/chiral phosphoric acid catalysis. A variety of alkyne-tethered indoles are suitable for this process. Mechanistic studies suggest that the insitu generated silver(I) chiral phosphate activates both the alkyne and the indole nucleophile in the initial cyclization step through an intermolecular hydrogen bond and the phosphate anion promotes proton transfer. In addition, further modifications of the cyclization products enabled stereochemistry-function studies of a series of bioactive indolines.

引用

页码：12206 / 12209

页数：4

共 20 条

[1] Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis
Wei, Hanlin
Bao, Ming
Dong, Kuiyong
Qiu, Lihua
Wu, Bing
Hu, Wenhao
Xu, Xinfang
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (52) : 17200 - 17204
[2] Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles
James, Michael J.
Clubley, Rosa E.
Palate, Kleopas Y.
Procter, Thomas J.
Wyton, Anthony C.
O'Brien, Peter
Taylor, Richard J. K.
Unsworth, William. P.
[J]. ORGANIC LETTERS, 2015, 17 (17) : 4372 - 4375
[3] Silver(I)-Catalyzed Enyne Cyclization/Aromatization of Alkyne-Tethered Cyclohexadienones to Access Meta-Substituted Phenols
Munakala, Anandarao
Chegondi, Rambabu
[J]. ORGANIC LETTERS, 2021, 23 (02) : 317 - 323
[4] Highly chemo- and enantioselective arylative cyclization of alkyne-tethered electron-deficient olefins catalyzed by rhodium complexes with chiral dienes
Shintani, R
Tsurusaki, A
Okamoto, K
Hayashi, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) : 3909 - 3912
[5] One-Pot Tandem Michael Addition/Enantioselective Conia-Ene Cyclization Mediated by Chiral Iron(III)/Silver(I) Cooperative Catalysis
Horibe, Takahiro
Sakakibara, Masato
Hiramatsu, Rin
Takeda, Kazuki
Ishihara, Kazuaki
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (38) : 16470 - 16474
[6] Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols
Banerjee, Debasis
Junge, Kathrin
Beller, Matthias
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) : 13049 - 13053
[7] Tandem thiyl radical addition and cyclization of chiral hydrazones using a silicon-tethered alkyne
Friestad, GK
Jiang, T
Fioroni, GM
[J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (19) : 2853 - 2856
[8] Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
Rawat, Vishal Kumar
Higashida, Kosuke
Sawamura, Masaya
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (06) : 1631 - 1637
[9] Enantioselective Synthesis of Tetrahydroquinolines by Borrowing Hydrogen Methodology: Cooperative Catalysis by an Achiral Iridacycle and a Chiral Phosphoric Acid
Lim, Ching Si
Thanh Truong Quach
Zhao, Yu
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) : 7176 - 7180
[10] Construction of Axially Chiral Indoles by Cycloaddition-Isomerization via Atroposelective Phosphoric Acid and Silver Sequential Catalysis
Wang, Yingcheng
Zhou, Xue
Shan, Wenyu
Liao, Ruisong
Deng, YuHua
Peng, Fangzhi
Shao, Zhihui
[J]. ACS CATALYSIS, 2022, 12 (13) : 8094 - 8103

← 1 2 →