Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

2015 ◽  
Vol 13 (13) ◽  
pp. 3982-3987 ◽  
Author(s):  
Jie Zhang ◽  
Ying Shao ◽  
Yaxiong Wang ◽  
Huihuang Li ◽  
Dongmei Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Amino Acid Esters ◽  
Dimethyl Malonate ◽  
Metal Free ◽  
New Strategy ◽  
Efficient Construction ◽  
Acid Esters

A new strategy has been developed for the synthesis of α-amino acid esters via a tandem hydrolysis/decarboxylation/nucleophilic substitution using TBAI/TBHP.

ChemInform Abstract: Transition-Metal-Free Decarboxylation of Dimethyl Malonate: An Efficient Construction of α-Amino Acid Esters Using TBAI/TBHP.

ChemInform ◽  
2015 ◽  
Vol 46 (29) ◽  
pp. no-no
Author(s):  
Jie Zhang ◽  
Ying Shao ◽  
Yaxiong Wang ◽  
Huihuang Li ◽  
Dongmei Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Amino Acid Esters ◽  
Dimethyl Malonate ◽  
Metal Free ◽  
Efficient Construction ◽  
Acid Esters

Metal free highly efficient C–N bond formation through 1,6-addition: synthesis and photophysical studies of diaryl methyl amino acid esters (DMAAEs)

2020 ◽  
Vol 44 (35) ◽  
pp. 14859-14864
Author(s):  
Deblina Roy ◽  
Abhineet Verma ◽  
Arpita Banerjee ◽  
Satyen Saha ◽  
Gautam Panda
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Bond Formation ◽  
Amino Acid Esters ◽  
Quinone Methides ◽  
One Pot ◽  
Metal Free ◽  
Photophysical Studies ◽  
The One ◽  
Acid Esters

A transition-metal free, proficient strategy for the one-pot synthesis of diverse diaryl methyl amino acid esters (DMAAEs) has been established from the easily accessible chiral amino acid esters and para-quinone methides (QMs) in very good to excellent yields.

ChemInform Abstract: A New Strategy for the Construction of α-Amino Acid Esters via Decarboxylation.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Jie Zhang ◽  
Jiewen Jiang ◽  
Yuling Li ◽  
Yun Zhao ◽  
Xiaobing Wan
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
New Strategy ◽  
Acid Esters

scholarly journals The reactions of α-amino acids and α-amino acid esters with high valent transition metal halides: synthesis of coordination complexes, activation processes and stabilization of α-ammonium acylchloride cations

RSC Advances ◽  
2017 ◽  
Vol 7 (17) ◽  
pp. 10158-10174 ◽  
Author(s):  
Lorenzo Biancalana ◽  
Marco Bortoluzzi ◽  
Eleonora Ferretti ◽  
Mohammad Hayatifar ◽  
Fabio Marchetti ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Transition Metal ◽  
Transition Metals ◽  
Coordination Compounds ◽  
Coordination Complexes ◽  
Amino Acid Esters ◽  
Metal Halides ◽  
High Valent ◽  
Acid Esters

We describe the synthesis of rare coordination compounds of early transition metals with α-amino acids and α-amino acid esters, the unusual C–C dimerization ofl-proline, and the stabilization of reactive α-ammonium acylchloride cations.

scholarly journals Catalytic Asymmetric Amino Acid and Its Derivatives by Chiral Aldehyde Catalysis

2021 ◽  
Vol 9 ◽  
Author(s):  
Kaijin Lin ◽  
Ang Shi ◽  
Chunhong Shi ◽  
Jinbiao Lin ◽  
Honggui Lin
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Catalytic System ◽  
Chemical Process ◽  
Amino Acid Esters ◽  
Asymmetric Reaction ◽  
Catalytic Systems ◽  
Catalytic Activation ◽  
The Face ◽  
Acid Esters

Amine acid transformation is an important chemical process in biological systems. As a well-developed and acknowledged tool, chiral aldehyde catalysis provides good catalytic activation and stereoselective control abilities in the asymmetric reaction of N-unprotected amino acid esters and amino acid esters analogs, in which the key to success is the design of the catalysts derived from chiral BINOL aldehyde, which is based on the face control of enolate intermediates. In this review, one of the co-catalytic systems that combined with a transition metal to form a multiplex catalytic system and the well-established multiplex stereocenters of chiral aldehyde catalysis have been reviewed. Finally, a novel organocatalysis is prospected.

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.

ChemInform Abstract: Metal-Free Direct Amidation of Peptidyl Thiol Esters with α-Amino Acid Esters.

ChemInform ◽  
2012 ◽  
Vol 43 (9) ◽  
pp. no-no
Author(s):  
Hao Chen ◽  
Maomao He ◽  
Yaya Wang ◽  
Linhui Zhai ◽  
Yongbo Cui ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Metal Free ◽  
Thiol Esters ◽  
Direct Amidation ◽  
Acid Esters
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