Asymmetric imine-ene reactions with chiral glyoxylate-derived α-imino esters: An efficient route to asymmetric synthesis of α-amino acids

1993 ◽  
Vol 34 (30) ◽  
pp. 4841-4842 ◽  
Author(s):  
Koichi Mikami ◽  
Masami Kaneko ◽  
Tomoko Yajima
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Ene Reactions ◽  
Efficient Route ◽  
Imino Esters

In the Pursuit of (Ald)Imine Surrogates for the Direct Asymmetric Synthesis of Non-Proteinogenic α-Amino Acids

Synthesis ◽  
2021 ◽  
Author(s):  
Stéphane P. Roche
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Substitution ◽  
Posttranslational Modifications ◽  
Kinetic Studies ◽  
Structural Diversity ◽  
Building Blocks ◽  
Bioactive Molecules ◽  
Biological Functions ◽  
Imino Esters

Nature remarkably employs posttranslational modifications of the 20 canonical α-amino acids to devise a far larger structural, conformational, and functional diversity found in non-proteinogenic amino acids (NPAAs) which ultimately translates into a plethora of complex biological functions. Synthetic chemists are continuously trying to reproduce and even extrapolate the repertoire of NPAA building blocks to build structural diversity into bioactive molecules and materials. The direct asymmetric functionalization of α-imino esters represents one of the most robust and attractive routes to NPAAs. This review summarizes the most prominent examples of bench-stable (ald)imine surrogates exploited for the synthesis of NPAAs including our most recent results in the nucleophilic substitution of α-haloglycines and other α-haloaminals. A synopsis of kinetic studies, reaction optimizations, and enantioselective catalytic methods is also presented.

Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2′,6′-dimethyl-tyrosines

1997 ◽  
Vol 38 (29) ◽  
pp. 5135-5138 ◽  
Author(s):  
Yinglin Han ◽  
Subo Liao ◽  
Wei Qiu ◽  
Chaozhong Cai ◽  
Victor J. Hruby
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Constrained Amino Acids

ChemInform Abstract: Asymmetric Synthesis via Heterocyclic Intermediates. Part 52. Synthesis of tert-Leucine and Related Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 24 (46) ◽  
pp. no-no
Author(s):  
U. GROTH ◽  
T. HUHN ◽  
B. PORSCH ◽  
C. SCHMECK ◽  
U. SCHOELLKOPF
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis

ChemInform Abstract: Asymmetric Synthesis of Trifluoromethyl-Piperidine Based γ-Amino Acids and of Trifluoromethyl-Indolizidines.

ChemInform ◽  
2013 ◽  
Vol 44 (24) ◽  
pp. no-no
Author(s):  
Wahid Bux Jatoi ◽  
Agnes Desiront ◽  
Aurelie Job ◽  
Yves Troin ◽  
Jean-Louis Canet
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis
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