Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids

被引：157

作者：

Metz, Alison E. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 01期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; PHASE-TRANSFER CATALYSTS; SUBSTITUTED NITROACETATES; 4+2 CYCLOADDITION; MICHAEL ADDITION; ALDOL REACTION; ALKYLATION; AMINATION; 1,4-ADDITION; CONSTRUCTION;

D O I：

10.1021/jo502408z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Because of their greater stability and unique conformational properties, unnatural amino acids are highly valued by pharmaceutical, biological, and organic chemists. This synopsis surveys the various catalytic methods used to access enantioenriched, acyclic a,a-disubstituted a-amino acids with a focus on the processes developed since 2007, when the last major reviews in this area were published.

引用

页码：1 / 7

页数：7

共 72 条

[1]

Alba A. R., 2010, CHEM-EUR J, P5354

[2] Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids [J].

Alba, Andrea-Nekane R. ;

Valero, Guillem ;

Calbet, Teresa ;

Font-Bardia, Merce ;

Moyano, Albert ;

Rios, Ramon .

NEW JOURNAL OF CHEMISTRY, 2012, 36 (03) :613-618

[3] Enantioselective Synthesis of α-Alkyl, α-Vinyl Amino Acids via [2,3]-Sigmatropic Rearrangement of Selenimides [J].

Armstrong, Alan ;

Emmerson, Daniel P. G. .

ORGANIC LETTERS, 2011, 13 (05) :1040-1043

[4] Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (-)-Trigonoliimine A [J].

Buyck, Thomas ;

Wang, Qian ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) :12714-12718

[5] Organocatalytic asymmetric synthesis of α,α-disubstituted α-amino acids and derivatives [J].

Cabrera, Silvia ;

Reyes, Efraim ;

Aleman, Jose ;

Milelli, Andrea ;

Kobbelgaard, Sara ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) :12031-12037

[6] Organocatalytic Asymmetric Michael Addition of Oxazolones to Arylsulfonyl Indoles: Facile Access to syn-Configured α,β-Disubstituted Tryptophan Derivatives [J].

Cai, Chang-Wu ;

Zhu, Xing-Li ;

Wu, Song ;

Zuo, Zong-Le ;

Yu, Liang-Liang ;

Qin, Da-Bin ;

Liu, Quan-Zhong ;

Jing, Lin-Hai .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) :456-459

[7] Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids [J].

Cativiela, Carlos ;

Ordonez, Mario .

TETRAHEDRON-ASYMMETRY, 2009, 20 (01) :1-63

[8] Asymmetric Synthesis of α-Allyl-α-Aryl α-Amino Acids by Tandem Alkylation/π-Allylation of α-Iminoesters [J].

Curto, John M. ;

Dickstein, Joshua S. ;

Berritt, Simon ;

Kozlowski, Marisa C. .

ORGANIC LETTERS, 2014, 16 (07) :1948-1951

[9] A Dual-Catalysis Approach to the Asymmetric Steglich Rearrangement and Catalytic Enantioselective Addition of O-Acylated Azlactones to Isoquinolines [J].

De, Chandra Kanta ;

Mittal, Nisha ;

Seidel, Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) :16802-16805

[10] Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center [J].

De Fusco, Claudia ;

Fuoco, Tiziana ;

Croce, Gianluca ;

Lattanzi, Alessandra .

ORGANIC LETTERS, 2012, 14 (16) :4078-4081

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