Organoboron Initiated Rh-Catalyzed Asymmetric Cascade Reactions: A Subtle Switch in Regioselectivity Leading to Chiral 3-Benzazepine Derivatives

被引：36

作者：

Claraz, Aurelie ^{[1
]}

Serpier, Fabien ^{[1
]}

Darses, Sylvain ^{[1
]}

机构：

[1] PSL Res Univ, Chim ParisTech CNRS, Inst Rech Chim Paris, 11 Rue Pierre & Marie Curie, F-75005 Paris, France

来源：

ACS CATALYSIS | 2017年 / 7卷 / 05期

关键词：

benzazepines; cascade reaction; carbocyclization; asymmetric catalysis; rhodium; organoboranes; ENANTIOSELECTIVE ARYLATIVE CYCLIZATION; ARYLBORONIC ACIDS; EFFICIENT SYNTHESIS; TANDEM TRANSFORMATIONS; RHODIUM; ALKYNES; ACCESS; AMINES; DESYMMETRIZATION; CARBOPALLADATION;

D O I：

10.1021/acscatal.7b00511

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：

An addition-carbocyclization cascade reaction initiated by arylboronic acids and catalyzed by a rhodium/chiral diene complex is described. Starting from N-bridged yne-enoate derivatives, chiral functionalized seven-membered 3-benzazepine heterocycles were obtained with high enantioselectivities, thanks to a rhodium 1,4-shift.

引用

页码：3410 / 3413

页数：4

共 69 条

[1] Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids [J].

Arcadi, Antonio ;

Aschi, Massimiliano ;

Chiarini, Marco ;

Ferrara, Giovanni ;

Marinelli, Fabio .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :493-498

[2] Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aidol cyclization [J].

Bocknack, BM ;

Wang, LC ;

Krische, MJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5421-5424

[3] Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].

Cauble, DF ;

Gipson, JD ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111

[4] Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates [J].

Crecente-Campo, Jose ;

Pilar Vazquez-Tato, M. ;

Seijas, Julio A. .

TETRAHEDRON, 2009, 65 (13) :2655-2659

[5] Calcium-Catalyzed Synthesis of 1,2-Disubstituted 3-Benzazepines [J].

Damsen, Helena ;

Niggemann, Meike .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (36) :7880-7883

[6] Efficient synthesis of the 3-benzazepine framework via intramolecular heck reductive cyclization [J].

Donets, Pavel A. ;

Van der Eycken, Erik V. .

ORGANIC LETTERS, 2007, 9 (16) :3017-3020

[7] An Asymmetric Approach towards (-)-Aphanorphine and Its Analogues [J].

Donets, Pavel A. ;

Goeman, Jan L. ;

Van der Eycken, Johan ;

Robeyns, Koen ;

Van Meervelt, Luc ;

Van der Eycken, Erik V. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (06) :793-796

[8]

FIDALGO J, 1994, HETEROCYCLES, V39, P581

[9] Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines [J].

Fuchs, JR ;

Funk, RL .

ORGANIC LETTERS, 2001, 3 (21) :3349-3351

[10] Efficient synthesis of trisubstituted alkenes in an aqueous-organic system using a versatile and recyclable Rh/m-TPPTC catalyst [J].

Genin, E ;

Michelet, V ;

Genêt, JP .

TETRAHEDRON LETTERS, 2004, 45 (21) :4157-4161

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