Negishi cross-couplings in the synthesis of amino acids

被引：43

作者：

Brittain, William D. G. ^{[1
]}

Cobb, Steven L. ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, South Rd, Durham DH1 3LE, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 01期

基金：

英国生物技术与生命科学研究理事会;

关键词：

ASYMMETRIC-SYNTHESIS; ORGANOZINC REAGENTS; CHIRAL AUXILIARY; DERIVATIVES; DISCOVERY; DESMOSINE; CHLORIDES; PEPTIDES; PROTEIN; DESIGN;

D O I：

10.1039/c7ob02682j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Negishi cross-coupling is a powerful C-C bond-forming reaction widely utilised in many areas of organic synthesis. This review details the use of Negishi cross-couplings in the synthesis of unnatural amino acids. The application of this reaction in the preparation of aromatic, heteroaromatic, and, complex amino acid derivatives are reviewed and presented herein.

引用

页码：10 / 20

页数：11

共 85 条

[1] Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents [J].

Agarwal, Devesh S. ;

Anantaraju, Hasitha Shilpa ;

Sriram, Dharmarajan ;

Yogeeswari, Perumal ;

Nanjegowda, Shankara H. ;

Mallu, P. ;

Sakhuja, Rajeev .

STEROIDS, 2016, 107 :87-97

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions [J].

Bartrum, Hannah E. ;

Adams, Harry ;

Caggiano, Lorenzo ;

Jackson, Richard F. W. .

TETRAHEDRON, 2008, 64 (17) :3701-3712

[4] Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide alkyne cycloadditions [J].

Brittain, William D. G. ;

Buckley, Benjamin R. ;

Fossey, John S. .

CHEMICAL COMMUNICATIONS, 2015, 51 (97) :17217-17220

[5] IDENTIFICATION OF AN ELASTIN CROSS-LINKING DOMAIN THAT JOINS 3 PEPTIDE CHAINS - POSSIBLE ROLE IN NUCLEATED ASSEMBLY [J].

BROWNAUGSBURGER, P ;

TISDALE, C ;

BROEKELMANN, T ;

SLOAN, C ;

MECHAM, RP .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (30) :17778-17783

[6] New routes to β-cycloalkylalanine derivatives using serine-derived organozinc reagents [J].

Carrillo-Marquez, T ;

Caggiano, L ;

Jackson, RFW ;

Grabowska, U ;

Rae, A ;

Tozer, MJ .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (22) :4117-4123

[7] In vivo incorporation of unnatural amino acids to probe structure, dynamics, and ligand binding in a large protein by nuclear magnetic resonance spectroscopy [J].

Cellitti, Susan E. ;

Jones, David H. ;

Lagpacan, Leanna ;

Hao, Xueshi ;

Zhang, Qiong ;

Hu, Huiyong ;

Brittain, Scott M. ;

Brinker, Achim ;

Caldwell, Jeremy ;

Bursulaya, Badry ;

Spraggon, Glen ;

Brock, Ansgar ;

Ryu, Youngha ;

Uno, Tetsuo ;

Schultz, Peter G. ;

Geierstanger, Bernhard H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9268-9281

[8] Synthesis and properties of MIDA boronate containing aromatic amino acids: New peptide building blocks [J].

Colgin, Neil ;

Flinn, Tony ;

Cobb, Steven L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) :1864-1870

[9] Recent developments in fragment-based drug discovery [J].

Congreve, Miles ;

Chessari, Gianni ;

Tisi, Dominic ;

Woodhead, Andrew J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (13) :3661-3680

[10] The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724

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