Palladium- and Nickel-Catalyzed Alkenylation of Enolates

被引：75

作者：

Ankner, Tobias ^{[1
]}

Cosner, Casey C. ^{[2
]}

Helquist, Paul ^{[1
,3
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[2] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

[3] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 06期

基金：

美国国家科学基金会;

关键词：

catalysis; CC coupling; enantioselectivity; enolates; natural products; nickel; palladium; ENANTIOSPECIFIC TOTAL-SYNTHESIS; SARPAGINE INDOLE ALKALOIDS; ENANTIOSELECTIVE ALPHA-ARYLATION; STEREOSPECIFIC TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; TETHERED VINYL HALIDES; GENERAL-APPROACH; REFORMATSKY REAGENT; ARYL HALIDES; ZEROVALENT COMPLEXES;

D O I：

10.1002/chem.201202798

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Transition-metal-catalyzed alkenylation of enolates provides a direct method to synthesize broadly useful ,-unsaturated carbonyl compounds from the corresponding carbonyl compound and alkenyl halides. Despite being reported in the early seventies, this reaction class saw little development for many years. In the past decade, however, efforts to develop this reaction further have increased considerably, and many research groups have reported efficient coupling protocols, including enantioselective versions. These reactions most commonly employ palladium catalysts, but there are also some important reports using nickel. There are many examples of this powerful transformation being used in the synthesis of complex natural products.

引用

页码：1858 / 1871

页数：14

共 111 条

[51] Metal-Catalyzed α-Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond Functionalization [J].

Johansson, Carin C. C. ;

Colacot, Thomas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :676-707

[52] Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant [J].

Kopka, Ihor E. ;

Lin, Linus S. ;

Jewell, James P. ;

Lanza, Thomas J. ;

Fong, Tung M. ;

Shen, Chun-Pyn ;

Lao, Zhege J. ;

Ha, Sookhee ;

Castonguay, Laurie G. ;

Van der Ploeg, Lex ;

Goulet, Mark T. ;

Hagmann, William K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (16) :4757-4761

[53] ARYLATION AND 1-ALKENYLATION ON ALPHA-POSITION OF KETONES VIA TRIBUTYLTIN ENOLATES CATALYZED BY PALLADIUM COMPLEX [J].

KOSUGI, M ;

HAGIWARA, I ;

SUMIYA, T ;

MIGITA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (01) :242-246

[54] Intramolecular Diels-Alder Cycloaddition/Rearrangement Cascade of an Amidofuran Derivative for the Synthesis of (±)-Minfiensine [J].

Li, Gang ;

Padwa, Albert .

ORGANIC LETTERS, 2011, 13 (15) :3767-3769

[55] Enantioselective α-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel [J].

Liao, Xuebin ;

Weng, Zhiqiang ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :195-200

[56] An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)-talcarpine and (-)-anhydromacrosalhine-methine [J].

Liao, Xuebin ;

Zhou, Hao ;

Yu, Jianming ;

Cook, James M. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8884-8890

[57] A Concise Total Synthesis of (±)-Minfiensine [J].

Liu, Peijun ;

Wang, Juan ;

Zhang, Jiancun ;

Qiu, Fayang G. .

ORGANIC LETTERS, 2011, 13 (24) :6426-6428

[58] Regiospecific, enantiospecific total synthesis of the alkoxy-substituted indole bases, 16-epi-Na-methylgardneral, 11-methoxyaffinisine, and 11-methoxymacroline as well as the indole alkaloids alstophylline and macralstonine [J].

Liu, XX ;

Deschamp, JR ;

Cook, JM .

ORGANIC LETTERS, 2002, 4 (20) :3339-3342

[59] Enantiospecific total synthesis of the enantiomer of the indole alkaloid intermediate macroline [J].

Liu, XX ;

Zhang, CC ;

Liao, XB ;

Cook, JM .

TETRAHEDRON LETTERS, 2002, 43 (41) :7373-7377

[60] Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine [J].

Liu, XX ;

Wang, T ;

Xu, QG ;

Ma, CR ;

Cook, JM .

TETRAHEDRON LETTERS, 2000, 41 (33) :6299-6303

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