145774-77-2Relevant academic research and scientific papers
A new method for the preparation of functionalized unnatural α-H-α-amino acid derivatives
Hyett, David J.,Didonè, Mara,Milcent, Thierry J.A.,Broxterman, Quirinus B.,Kaptein, Bernard
, p. 7771 - 7774 (2007/10/03)
A new method for the preparation of α-H-α-amino acids is reported based on the α-alkylation of iminoacetic acid esters or amides. These imines are readily available by the reaction of glyoxylic acid esters with branched primary amines. The subsequent reaction with methanolic ammonia gave the corresponding iminoacetic acid amides. α-Alkylation of these imines with various electrophiles under basic conditions, followed by an acidic hydrolysis, gave α-amino acids, esters, or amides in up to 93% yield. α-Alkylation under chiral PTC conditions resulted in mono-alkylated amino acids with 90% ee.
PROCESS FOR THE PREPARATION OF AN α-AMINO CARBONYL COMPOUND
-
Page 15, (2008/06/13)
The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.
SYNTHESE DE DERIVES DE L'ACIDE PIPECOLIQUE PAR REACTION D'AZA-DIELS-ALDER : CYCLOADDITIONS ACTIVEES PAR L'IODURE DE ZINC ENTRE LA 1-(PHENYL)-ETHYLIMINE DU GLYOXYLATE DE METHYLE ET LES DIENES RICHES EN ELECTRONS
Abraham, Herve,Theus, Elisabeth,Stella, Lucien
, p. 361 - 366 (2007/10/02)
The methyl N-(1-phenylethyl)-α-iminoacetate undergoes zinc iodide activated aza-Diels-Alder cycloaddition reactions with electron rich conjugated dienes.Cyclic α-amino-acids are formed in good yields, with complete regioselectivity, but the extent of asymmetric induction by the chiral phenethyl group on the nitrogen is low. KEY WORDS: aza-Diels-Alder reactions; heterocyclic α-amino-acids
REACTION D'AZA-DIELS-ALDER DIASTEREOSELECTIVE: UTILISATION DE LA 1-PHENYLETHYL IMINE DE GLYOXYLATE D'ALKYLE POUR LA SYNTHESES DE DERIVES D'α-AMINO ACIDES CYCLIQUES
Abraham, Herve,Stella, Lucien
, p. 9707 - 9718 (2007/10/02)
The use of trifluoroacetic acid-boron trifluoride combination is highly effective in dichloromethane for the activation of 1-phenylethylimine of methyl or ethyl glyoxylates as heterodienophiles in Diels-Alder cycloaddition reactions with a series of conju
Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate
Stella,Abraham,Feneau-Dupont,Tinant,Declercq
, p. 2603 - 2606 (2007/10/02)
The Diels-Alder reaction between cyclopentadiene and the chiral 1-phenyl-ethyl imine of methyl glyoxylate takes place very easily by activation with trifluoroacetic acid and boron trifluoride etherate to provide diastereoselectively (total face selectivit
