Enantioselective synthesis of benzazepinoindoles bearing trifluoromethylated quaternary stereocenters catalyzed by chiral spirocyclic phosphoric acids

被引：54

作者：

Li, Xuejian ^{[1
]}

Chen, Di ^{[1
]}

Gu, Haorui ^{[1
]}

Lin, Xufeng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Asymmetr Catalysis & Synth, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 56期

关键词：

PICTET-SPENGLER REACTIONS; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; PERFLUOROALKYLATION; FLUORINATION; CYCLIZATION; CASCADE; ACCESS; COMBINATION; EPOXIDATION; EFFICIENT;

D O I：

10.1039/c4cc02295e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first highly enantioselective iso-Pictet-Spengler reaction of C-2-linked o-aminobenzylindoles with trifluoromethyl ketones was developed using chiral spirocyclic phosphoric acids as organocatalysts, which afforded optically active benzazepinoindoles bearing trifluoromethylated quaternary stereocenters.

引用

页码：7538 / 7541

页数：4

共 79 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2] Organocatalytic Asymmetric Synthesis of Chiral Pyrrolizines by Cascade Conjugate Addition-Aldol Reactions [J].

Bae, Ju-Yeon ;

Lee, Hyo-Jun ;

Youn, Seok-Ho ;

Kwon, Su-Hyun ;

Cho, Chang-Woo .

ORGANIC LETTERS, 2010, 12 (19) :4352-4355

[3] The chemistry of trifluoromethyl imines and related acetals derived from fluoral [J].

Bégué, JP ;

Bonnet-Delpon, D ;

Crousse, B ;

Legros, J .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) :562-572

[4] Highly Enantioselective Pictet-Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides [J].

Bou-Hamdan, Farhan R. ;

Leighton, James L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) :2403-2406

[5] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[6] An olefin isomerization/asymmetric Pictet-Spengler cascade via sequential catalysis of ruthenium alkylidene and chiral phosphoric acid [J].

Cai, Quan ;

Liang, Xiao-Wei ;

Wang, Shou-Guo ;

You, Shu-Li .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (10) :1602-1605

[7] Process research and development of an NK-1 receptor antagonist. enantioselective trifluoromethyl addition to a ketone in the preparation of a chiral isochroman [J].

Caron, Stephane ;

Do, Nga M. ;

Sieser, Janice E. ;

Arpin, Patrice ;

Vazquez, Enrique .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (06) :1015-1024

[8] Enantio- and Diastereoselective Assembly of Tetrahydrofuran and Tetrahydropyran Skeletons with All-Carbon-Substituted Quaternary Stereocenters [J].

Chen, Zhilong ;

Sun, Jianwei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) :13593-13596

[9] Catalytic Enantioselective Synthesis of Tetrahydroisoquinolines and Their Analogues Bearing a C4 Stereocenter: Formal Synthesis of (+)-(8S,13R)-Cyclocelabenzine [J].

Chen, Zhilong ;

Wang, Zhaobin ;

Sun, Jianwei .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) :8426-8430

[10] Complex Bioactive Alkaloid-Type Polycycles through Efficient Catalytic Asymmetric Multicomponent Aza-Diels-Alder Reaction of Indoles with Oxetane as Directing Group [J].

Chen, Zhilong ;

Wang, Beilei ;

Wang, Zhaobin ;

Zhu, Guangyu ;

Sun, Jianwei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) :2027-2031

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