81357-12-2

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 81357-08-6 benzyl (triphenyl-λ⁵-phosphanilidene)carbamate 
• 3422-03-5 benzyloxycarbonyl azide 
• 83026-98-6 N-carbobenzoxy-α-ethoxyglycine ethyl ester 
• 577973-96-7 N-Cbz-α-bromoglycine ethyl ester 

Downstream Products

• 81357-22-4 (1S,3S,4R)-2-Aza-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-benzyl ester 3-ethyl ester 
• 78553-48-7 ethyl (2S)-2-(benzyloxycarbonylamino)-4-pentenoate 

Relevant academic research and scientific papers

METHOD FOR ASYMMETRIC ALLYLATION OF α-IMINO ACID

A method for the asymmetric allylation of an α-imino acid, wherein an allylsilane compound is reacted with an an α-imino acid having a structure in which an oxycarbonyl group is bonded to a nitrogen atom of the imino group in the presence of a chiral copp

Catalytic, asymmetric Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen

(Matrix presented) Catalytic, enantioselective Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen are described. Several N-carbamate-protected α-imino esters, which are readily prepared from 2-bromoglycine esters using a polymer-supported amine, reacted with silicon enolates to afford the desired adducts in high yields with high enantioselectivity using a copper(II)-diamine complex. Easy deprotection of the product amine and transformation to free o-amino acid derivatives have also been demonstrated.

Optically active aromatic and heteroaromatic α-amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to α-imino esters

The development of a practical one-pot catalytic enantioselective procedure for the synthesis of non-natural aromatic and heteroaromatic α-amino acids is reported. Starting from readily available starting materials and application of a chiral BINAP-Cu(I) catalyst, the optically active products are formed with readily removable N-protecting groups. The scope of the reaction is demonstrated by the addition of substituted furans, thiophenes, pyrroles, and aromatic compounds to N-alkoxy-carbonyl-α-imino esters in good yields and with enantioselectivities up to 96% ee for the furans, 93% ee for the thiophenes, and 98% for the aromatic compounds. The protecting groups are readily removed, and various transformations of the aromatic and heteroaromatic a-amino acids are demonstrated. The coordination of the N-alkoxycarbonyl α-imino ester to the chiral BINAP-Cu(I) complex and the enantioselectivity of the catalyst is discussed on the basis of the DFT calculations and X-ray crystallographic data.

PREPARATION OF DI- AND TRIACYLIMINES AND THEIR USE IN THE SYNTHESIS OF NITROGEN HETEROCYCLES

Reaction of aza-Wittig reagents with glyoxylates and keto malonates produces di- and triacylimines which are moderately reactive dienophiles for Diels-Alder cycloaddition.