Accessing chemical diversity by stereoselective gold-catalyzed manipulation of allylic and propargylic alcohols

被引：25

作者：

Cera, Gianpiero ^{[1
]}

Chiarucci, Michel ^{[1
]}

Bandini, Marco ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy

来源：

PURE AND APPLIED CHEMISTRY | 2012年 / 84卷 / 08期

关键词：

asymmetric catalysis; gold; heterocyclic chemistry; INTERMOLECULAR REACTIONS; ORGANIC-REACTIONS; INDOLES; AU; ALKYLATION; COMPLEXES; ALKYNES; SUBSTITUTION; DERIVATIVES; CYCLIZATION;

D O I：

10.1351/PAC-CON-11-09-05

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The combined use of asymmetric Au(I) catalysis with allylic as well as propargylic alcohols proved to be a competent synthetic tool, toward the realization of complex molecular organic architectures in a stereochemically defined manner. In particular, allylic alcohols have been utilized as alkylating agents in the synthesis of tetrahydrocarbazoles/carbolines and morpholines by means of new C-C and C-X bond-forming processes. Analogously, the direct activation of indole-propargylic alcohols with cationic Au complexes opened a direct access to tetracyclic fused indolines in a highly stereoselective manner.

引用

页码：1673 / 1684

页数：12

共 62 条

[1]

[Anonymous], 2010, CATALYTIC ASYMMETRIC

[2]

[Anonymous], 2008, CHEM REV, V8, P2793

[3] Au-catalyzed cyclization of monoallylic diols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Biannic, Berenger .

ORGANIC LETTERS, 2008, 10 (04) :669-671

[4] Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry [J].

Aponick, Aaron ;

Biannic, Berenger .

ORGANIC LETTERS, 2011, 13 (06) :1330-1333

[5] A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes [J].

Aponick, Aaron ;

Biannic, Berenger ;

Jong, Michael R. .

CHEMICAL COMMUNICATIONS, 2010, 46 (36) :6849-6851

[6] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[7] Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation [J].

Bandini, M ;

Melloni, A ;

Piccinelli, F ;

Sinisi, R ;

Tommasi, S ;

Umani-Ronchi, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1424-1425

[8] A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].

Bandini, M ;

Melloni, A ;

Tommasi, S ;

Umani-Ronchi, A .

SYNLETT, 2005, (08) :1199-1222

[9] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[10] Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles [J].

Bandini, Marco ;

Gualandi, Andrea ;

Monari, Magda ;

Romaniello, Alessandro ;

Savoia, Diego ;

Tragni, Michele .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) :338-347

← 1 2 3 4 5 6 7 →