Gold(I)-catalyzed enantioselective bromocyclization reactions of allenes

被引：72

作者：

Miles, Dillon H. ^{[1
]}

Veguillas, Marcos ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

CHEMICAL SCIENCE | 2013年 / 4卷 / 09期

关键词：

INTRAMOLECULAR HYDROAMINATION; ELECTROPHILIC FLUORINATION; EFFICIENT PREPARATION; ORGANOGOLD COMPOUNDS; FACILE SYNTHESIS; CHIRAL ANIONS; ACID; BROMOLACTONIZATION; REACTIVITY; COMPLEXES;

D O I：

10.1039/c3sc50811k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective bromocyclization of allenes is accomplished through the use of a chiral dinuclear gold complex and/or chiral phosphate anions in the presence of an N-bromolactam as an electrophilic bromine source. This method provides access to heterocyclic vinyl bromides with an allylic stereocenter in excellent yield and enantioselectivity. These enantioenriched vinyl bromides may serve as a handle for further derivatization via cross-coupling reactions.

引用

页码：3427 / 3431

页数：5

共 62 条

[11] Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions [J].

Crone, Benedikt ;

Kirsch, Stefan F. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5435-5438

[12] Facile Synthesis of Monofluoro γ-Lactones and Pyrrolidine Derivatives via Electrophilic Fluorination of Allenoic Acids and Amides [J].

Cui Haifeng ;

Chai Zhuo ;

Zhao Gang ;

Zhu Shizheng .

CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (01) :189-194

[13] Gold-catalyzed synthesis of substituted 2-aminofurans via formal [4+1]-cycloadditions on 3-en-1-ynamides [J].

Dateer, Ramesh B. ;

Pati, Kamalkishore ;

Liu, Rai-Shung .

CHEMICAL COMMUNICATIONS, 2012, 48 (57) :7200-7202

[14] Catalytic, Asymmetric Halofunctionalization of Alkenes-A Critical Perspective [J].

Denmark, Scott E. ;

Kuester, William E. ;

Burk, Matthew T. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (44) :10938-10953

[15] Enantioselective Bromocycloetherification by Lewis Base/Chiral Bronsted Acid Cooperative Catalysis [J].

Denmark, Scott E. ;

Burk, Matthew T. .

ORGANIC LETTERS, 2012, 14 (01) :256-259

[16] Achiral Counterion Control of Enantioselectivity in a Bronsted Acid-Catalyzed Iodolactonization [J].

Dobish, Mark C. ;

Johnston, Jeffrey N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (14) :6068-6071

[17] ORGANIC-SYNTHESIS USING SODIUM-BROMATE .2. A FACILE SYNTHESIS OF N-BROMO IMIDES AND AMIDES USING SODIUM-BROMATE AND HYDROBROMIC ACID (OR SODIUM-BROMIDE) IN THE PRESENCE OF SULFURIC-ACID [J].

FUJISAKI, S ;

HAMURA, S ;

EGUCHI, H ;

NISHIDA, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (08) :2426-2428

[18] Predicting Hydrogen-Bond Strengths from Acid-Base Molecular Properties. The pKa Slide Rule: Toward the Solution of a Long-Lasting Problem [J].

Gilli, Paola ;

Pretto, Loretta ;

Bertolasi, Valerio ;

Gilli, Gastone .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (01) :33-44

[19] Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold-Catalyzed Cyclization/Cross Coupling Sequence [J].

Gockel, Birgit ;

Krause, Norbert .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (02) :311-316

[20]

Hamilton GL, 2007, SCIENCE, V317, P496, DOI 10.1126/science.1145229

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