Enantioselective oxidative functionalization of the Csp3–H bond adjacent to a nitrogen atom for rapid access to β-hydroxyl-α-amino acid derivatives

2016 ◽  
Vol 52 (79) ◽  
pp. 11831-11833 ◽  
Author(s):  
Lin Qiu ◽  
Xin Guo ◽  
Yu Qian ◽  
Changcheng Jing ◽  
Chaoqun Ma ◽  
...  
Keyword(s):  
Amino Acid ◽  
Nitrogen Atom ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Oxidative Functionalization ◽  
Mild Conditions ◽  
Rapid Access

Highly chemoselective and enantioselective one-pot reactions involved in the oxidative functionalization of Csp3–H bonds adjacent to nitrogen atoms were developed to rapidly construct highly functionalized β-hydroxyl-α-amino acid derivatives from simple starting materials under mild conditions.

Synthesis of New Chiral 4,5,6,7-Tetrahydro[1,2,3]triazolo[1,5-a]pyrazines from α-Amino Acid Derivatives under Mild Conditions.

ChemInform ◽  
2007 ◽  
Vol 38 (48) ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Pradip K. Maity ◽  
Rajesh G. Gonnade ◽  
Mukund S. Chorghade ◽  
Mukund K. Gurjar
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Mild Conditions

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

One-Pot Asymmetric Synthesis of β-Cyanohydroxymethyl α-Amino Acid Derivatives:  Formation of Three Contiguous Stereogenic Centers

2002 ◽  
Vol 4 (25) ◽  
pp. 4519-4522 ◽  
Author(s):  
Shin-ichi Watanabe ◽  
Armando Córdova ◽  
Fujie Tanaka ◽  
Carlos F. Barbas
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Stereogenic Centers

One-pot synthesis of β-amino acid derivatives via addition of bis(O-silyl) ketene acetals on iminium salts

2007 ◽  
Vol 48 (47) ◽  
pp. 8277-8280 ◽  
Author(s):  
Roba Moumné ◽  
Bernard Denise ◽  
Andrée Parlier ◽  
Solange Lavielle ◽  
Henri Rudler ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Iminium Salts ◽  
One Pot Synthesis ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals

Iodine/K2CO3-catalyzed synthesis of multisubstituted pyrrolidine-2-carboxylates via a one-pot reaction between an araldehyde, an amino acid ester, and a chalcone

2019 ◽  
Vol 43 (3-4) ◽  
pp. 90-96
Author(s):  
Yongjian Zhang ◽  
Junyi Su ◽  
Tengfei Lin ◽  
Zhangqi Lin ◽  
Zichun Zhou ◽  
...  
Keyword(s):  
Amino Acid ◽  
Acid Ester ◽  
Amino Acid Ester ◽  
One Pot ◽  
Metal Free ◽  
Simple Operation ◽  
Mild Conditions

A series of more than 20 multisubstituted pyrrolidine-2-carboxylates were synthesized via a one-pot cycloaddition of an araldehyde, an amino acid ester, and a chalcone catalyzed by I2/K2CO3 in tetrahydrofuran at 80 °C. The advantages of this method are readily available starting materials, mild conditions, and simple operation, and it is metal free and yields are good to excellent.

One-Pot Synthesis of α-Halo β-Amino Acid Derivatives via the Difunctional Coupling of Ethyl α-Diazoacetate with Silyl Halides and N,O-Acetals or Aromatic Tertiary Amines

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1823-1832 ◽  
Author(s):  
Norio Sakai ◽  
Kazuki Sasaki ◽  
Hiroki Suzuki ◽  
Yohei Ogiwara
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Tertiary Amines ◽  
One Pot ◽  
Metal Free ◽  
Reaction Intermediate ◽  
One Pot Synthesis ◽  
Acid Esters ◽  
Three Component Coupling

The difunctionalization of ethyl α-diazoacetate (EDA) using silyl halides as a nucleophile and N,O-acetals as an electrophile under metal-free conditions is described. This process undergoes a novel three-component coupling (3-CC) reaction using EDA, which leads to a one-pot preparation of α-halo β-amino acid esters. Also, this protocol could be adapted to accept an electrophile composed of aromatic tertiary amines. In both 3-CC reactions, the key reaction intermediate is an iminium intermediate that can be easily and effectively generated either from N,O-acetals or from aromatic tertiary amines.

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