Formation of Flavor Components by the Reaction of Amino Acid and Carbonyl Compounds in Mild Conditions

2000 ◽  
Vol 48 (9) ◽  
pp. 3761-3766 ◽  
Author(s):  
Laura Pripis-Nicolau ◽  
Gilles de Revel ◽  
Alain Bertrand ◽  
Alain Maujean
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Mild Conditions ◽  
Flavor Components

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

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

Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of α-amino acids and α-amino methyl esters

2002 ◽  
Vol 80 (7) ◽  
pp. 779-788 ◽  
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Elena Pol ◽  
Angelo G Giumanini
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Sodium Borohydride ◽  
Carbonyl Compounds ◽  
Condensation Reaction ◽  
Methyl Esters ◽  
Reducing Agent ◽  
Reductive Condensation ◽  
Versatile Reagent

α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

ChemInform Abstract: A SYNTHESIS OF N-PHTHALOYL AMINO ACIDS AND AMINO ACID ESTERS UNDER MILD CONDITIONS

1973 ◽  
Vol 4 (40) ◽  
pp. no-no
Author(s):  
D. A. HOOGWATER ◽  
D. N. REINHOUDT ◽  
T. S. LIE ◽  
J. J. GUNNEWEG ◽  
H. C. BEYERMAN
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Esters ◽  
Mild Conditions ◽  
Acid Esters

In Situ Generation of Brønsted Acidity in the Pd-I Bifunctional Catalysts for Selective Reductive Etherification of Carbonyl Compounds under Mild Conditions

ACS Catalysis ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 2940-2948 ◽  
Author(s):  
Dan Wu ◽  
Willinton Y. Hernández ◽  
Songwei Zhang ◽  
Evgeny I. Vovk ◽  
Xiaohong Zhou ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Bifunctional Catalysts ◽  
Brønsted Acidity ◽  
Mild Conditions ◽  
Brönsted Acidity ◽  
In Situ Generation

Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols

2020 ◽  
Vol 10 (17) ◽  
pp. 5945-5952
Author(s):  
Hongyue Wang ◽  
Ge Qu ◽  
Jun-Kuan Li ◽  
Jun-An Ma ◽  
Jinggong Guo ◽  
...  
Keyword(s):  
Data Mining ◽  
Amino Acid ◽  
Carbonyl Compounds ◽  
Amino Alcohols ◽  
Chiral Amino Alcohols

Five amine dehydrogenases (AmDHs) derived from amino acid dehydrogenases have been identified and evaluated for the stereoselective amination of α-/β-functionalized carbonyl compounds to synthesize chiral amino alcohols.

scholarly journals Acrylamide Formation in Food: A Mechanistic Perspective

2005 ◽  
Vol 88 (1) ◽  
pp. 262-267 ◽  
Author(s):  
Varoujan A Yaylayan ◽  
Richard H Stadler
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Azomethine Ylide ◽  
Significant Progress ◽  
Acid Moiety ◽  
Sugar Moiety ◽  
Acrylamide Formation ◽  
Amino Acid Moiety ◽  
Strecker Aldehyde

Abstract Earliest reports on the origin of acrylamide in food have confirmed asparagine as the main amino acid responsible for its formation. Available evidence suggests that sugars and other carbonyl compounds play a specific role in the decarboxylation process of asparagine, a necessary step in the generation of acrylamide. It has been proposed that Schiff base intermediate formed between asparagine and the sugar provides a low energy alternative to the decarboxylation from the intact Amadori product through generation and decomposition of oxazolidin-5-one intermediate, leading to the formation of a relatively stable azomethine ylide. Literature data indicate the propensity of such protonated ylides to undergo irreversible 1,2-prototropic shift and produce, in this case, decarboxylated Schiff bases which can easily rearrange into E Decarboxylated Amadori products can either undergo the well known β-elimination process initiated by the sugar moiety to produce 3-aminopropanamide and 1-deoxyglucosone or undergo 1,2-elimination initiated by the amino acid moiety to directly generate acrylamide. On the other hand, the Schiff intermediate can either hydrolyze and release 3-aminopropanamide or similarly undergo amino acid initiated 1,2-elimination to directly form acrylamide. Other thermolytic pathways to acrylamide—considered marginal at this stage—via the Strecker aldehyde, acrolein, and acrylic acid, are also addressed. Despite significant progress in the understanding of the mechanistic aspects of acrylamide formation, concrete evidence for the role of the different proposed intermediates in foods is still lacking.

Guanylation/cyclisation of amino acid esters using an imidazolin-2-iminato titanium initiator

2019 ◽  
Vol 48 (21) ◽  
pp. 7227-7235 ◽  
Author(s):  
Suman Das ◽  
Jayeeta Bhattacharjee ◽  
Tarun K. Panda
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Urea Derivatives ◽  
Mild Conditions ◽  
Acid Esters

Catalytic hydroamination of amino acid esters with carbodiimides and isocyanates to furnish corresponding quinazolinone and urea derivatives using two TiIV complexes under mild conditions is reported.

Sign in / Sign up

Export Citation Format

Share Document