ChemInform Abstract: Improved Preparation of Enantiomerically Pure 5-Oxo Amino Acid Derivatives by Palladium Catalyzed Coupling Reactions.

The preparation of enantiomerically pure N-tert-butyloxycarbonyl,N-methylamino acids by N-methylation of the parent amino acid derivatives using sodium hydride and methyl iodide in tetrahydrofuran at room temperature is described for neutral amino acids including O-benzyl-protected threonine and tyrosine. Methylation of the O-benzylserine derivative under these conditions gives the N-methyldehydroalanine derivative. The β-elimination is completely suppressed, giving the corresponding N-methylserine derivative when the reaction is carried out at 5 °C. Other related data on N-methylation and N-methylamino acid derivatives are presented.

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Palladium-Catalyzed Intermolecular Aminocarbonylation of Alkenes: Efficient Access of β-Amino Acid Derivatives

Journal of the American Chemical Society ◽

10.1021/jacs.5b00719 ◽

2015 ◽

Vol 137 (7) ◽

pp. 2480-2483 ◽

Cited By ~ 91

Author(s):

Jiashun Cheng ◽

Xiaoxu Qi ◽

Ming Li ◽

Pinhong Chen ◽

Guosheng Liu

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Efficient Access ◽

Palladium Catalyzed

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Palladium-Catalyzed Regio- and Stereoselective Cross-Coupling of Vinylethylene Carbonates with Ketimine Esters to Generate (Z)-Tri- and Tetra-substituted Allylic Amino Acid Derivatives

Organic Letters ◽

10.1021/acs.orglett.0c01211 ◽

2020 ◽

Vol 22 (11) ◽

pp. 4135-4140

Author(s):

Miaolin Ke ◽

Zhigang Liu ◽

Guanxin Huang ◽

Jiaqi Wang ◽

Yuan Tao ◽

...

Keyword(s):

Amino Acid ◽

Cross Coupling ◽

Amino Acid Derivatives ◽

Palladium Catalyzed

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Synthesis of Chiral β-Fluoroalkyl β-Amino Acid Derivatives via Palladium-Catalyzed Hydrogenation

The Journal of Organic Chemistry ◽

10.1021/acs.joc.9b01523 ◽

2019 ◽

Vol 84 (16) ◽

pp. 10371-10379 ◽

Cited By ~ 2

Author(s):

Mu-Wang Chen ◽

Qin Yang ◽

Zhihong Deng ◽

Qiuping Ding ◽

Yiyuan Peng

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Palladium Catalyzed

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Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives

Nature Communications ◽

10.1038/s41467-019-13326-8 ◽

2019 ◽

Vol 10 (1) ◽

Cited By ~ 2

Author(s):

Kostiantyn O. Marichev ◽

Kuiyong Dong ◽

Lynée A. Massey ◽

Yongming Deng ◽

Luca De Angelis ◽

...

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Coupling Reactions ◽

Central Importance ◽

Bond Forming ◽

Donor Acceptor ◽

High Yields ◽

High Degree ◽

Oxygen Bond ◽

Steric Selectivity

AbstractCoupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor–acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine.

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