Biomimetic, Reducing Agent-Free Reductive Amination of Fluorocarbonyl Compounds: Practical Asymmetric Synthesis of Enantiopure Fluoroamines and Amino Acids

1999 ◽  
pp. 74-83 ◽  
Author(s):  
Vadim A. Soloshonok
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Reductive Amination ◽  
Reducing Agent

Aminobenzylation d'aldéhydes phosphoniques: préparation d'acides aminoalkylphosphoniques

1981 ◽  
Vol 59 (19) ◽  
pp. 2864-2869 ◽  
Author(s):  
Geneviève Fabre ◽  
Noël Collignon ◽  
Philippe Savignac
Keyword(s):  
Amino Acids ◽  
Catalytic Hydrogenation ◽  
Reductive Amination ◽  
Reducing Agent ◽  
Amino Esters ◽  
Hydrolysis Of

The reaction of phosphonic aldehydes with benzylamine in presence of NaBH3CN yields benzylaminoalkylphosphonates which, submitted to catalytic hydrogenation, lead to phosphonic amino esters. When reductive amination is carried out with H2/Pd reduction and debenzylation are observed simultaneously. In the absence of reducing agent the enaminobenzylphosphonate can be isolated and N-alkylated. Hydrolysis of phosphonic amino-esters with dilute HCl gives phosphonic amino acids. The order of occurrence of each operation, as well as the choice of the catalyst is discussed.

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

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.

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