Design and Enantioselective Synthesis of β-Vinyl Tryptamine Building Blocks for Construction of Privileged Chiral Indole Scaffolds

被引：21

作者：

Lin, Tao-Yan ^{[1
]}

Wu, Hai-Hong ^{[1
]}

Feng, Jian-Jun ^{[1
]}

Zhang, Junliang ^{[1
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China

来源：

ACS CATALYSIS | 2017年 / 7卷 / 06期

基金：

中国国家自然科学基金;

关键词：

rhodium; vinylaziridines; tryptamines; chirality transfer; diversity-oriented synthesis; allylic substitution reaction; ORGANOCATALYTIC MICHAEL ADDITION; NONREARRANGED MONOTERPENOID UNIT; CATALYZED ALLYLIC ALKYLATIONS; FRIEDEL-CRAFTS ALKYLATION; RING-OPENING REACTIONS; ASYMMETRIC-SYNTHESIS; LEWIS-ACID; ISATYLIDENE-3-ACETALDEHYDES APPLICATION; INTERMOLECULAR CYCLOADDITIONS; NITROGEN-HETEROCYCLES;

D O I：

10.1021/acscatal.7b00870

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The highly efficient and stereo-specific synthesis of the enantioenriched versatile building blocks-namely, beta-vinyl-tryptamines-by rhodium-catalyzed allylic substitutions of vinylaziridines and indoles is presented. Besides indoles, pyrroles can also serve as competent carbon nucleophiles in the current reaction, which is different from the previous works. To demonstrate the synthetic utility of our method, up to 11 natural product and pharmaceutically relevant chiral indole scaffolds were synthesized in highly efficient reaction sequences. Notably, asymmetric formal synthesis of a potent constrained analogue of MS-245 and a nNOS and 5-HT1B/1D receptor inhibitor are also reported

引用

收藏

页码：4047 / 4052

页数：6

相关论文

共 71 条

[1] Reaction of 3-(1-arylsulfonylalkyl)-indoles with easily enolisable derivatives promoted by potassium fluoride on basic alumina [J].

Ballini, Roberto ;

Palmieri, Alessandro ;

Petrini, Marino ;

Shaikh, Rafik R. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) :129-134

[2] New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic subsitution: Controlling the regioselectivity [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ORGANIC LETTERS, 2004, 6 (18) :3199-3202

[3] Generating diverse skeletons of small molecules combinatorially [J].

Burke, MD ;

Berger, EM ;

Schreiber, SL .

SCIENCE, 2003, 302 (5645) :613-618

[4] Copper(I)-Catalyzed Kinetic Resolution of N-Sulfonylaziridines with Indoles: Efficient Construction of Pyrroloindolines [J].

Chai, Zhuo ;

Zhu, You-Min ;

Yang, Pei-Jun ;

Wang, Shaoyin ;

Wang, Shaowu ;

Liu, Zhen ;

Yang, Gaosheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) :10088-10091

[5] Enantioselective Direct Functionalization of Indoles by Pd/Sulfoxide-Phosphine-Catalyzed N-Allylic Alkylation [J].

Chen, Li-Yan ;

Yu, Xiao-Ye ;

Chen, Jia-Rong ;

Feng, Bin ;

Zhang, Hong ;

Qi, Ying-Hua ;

Xiao, Wen-Jing .

ORGANIC LETTERS, 2015, 17 (06) :1381-1384

[6] Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction [J].

de Graaff, Corien ;

Bensch, Lisa ;

Boersma, Sjoerd J. ;

Cioc, Razvan C. ;

van Lint, Matthijs J. ;

Janssen, Elwin ;

Turner, Nicholas J. ;

Orru, Romano V. A. ;

Ruijter, Eelco .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :14133-14136

[7] From Nature to Drug Discovery: The Indole Scaffold as a 'Privileged Structure' [J].

de Sa Alves, Fernando Rodrigues ;

Barreiro, Eliezer J. ;

Manssour Fraga, Carlos Alberto .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2009, 9 (07) :782-793

[8] Rhodium-Catalyzed Allylic Substitution with an Acyl Anion Equivalent: Stereospecific Construction of Acyclic Quaternary Carbon Stereogenic Centers [J].

Evans, P. Andrew ;

Oliver, Samuel ;

Chae, Jungha .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (47) :19314-19317

[9] Conservation of absolute configuration in the acyclic rhodium-catalyzed allylic alkylation reaction:: Evidence for an enyl (σ+π) organorhodium intermediate [J].

Evans, PA ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5581-5582

[10] Synthesis of Unsaturated N-Heterocycles by Cycloadditions of Aziridines and Alkynes [J].

Feng, Jian-Jun ;

Zhang, Junliang .

ACS CATALYSIS, 2016, 6 (10) :6651-6661

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