40781-29-1

Upstream product

• 62-53-3 aniline 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 29617-66-1 (S)-2-chloropropanoic acid 
• 17639-93-9 2-chloro-propionic acid methyl ester 

Relevant academic research and scientific papers

An unusual conformation of α-haloamides due to cooperative binding with zincated porphyrins

CD and NMR spectroscopic evidence of cooperative binding between an α-halogen atom and a carboxamide group with a zinc porphyrin leads to an unprecedented conformation for the determination of the absolute stereochemistry of α-haloamides (α-halocarboxylic acids derivatized with 1,4-phenylenediamine) through the use of exciton-coupled circular dichroism (ECCD). With the use of chiral lactams, whose rotomeric contributions are minimized, both ECCD and NMR spectroscopy demonstrate that the porphyrin favors binding to the side of the sterically more demanding halogen atom as compared to the smaller hydrogen atom. In all, the data is strongly suggestive of an unusual conformation not observed before for α-chiral amides. A mnemonic for determining the absolute stereochemistry of α-halogenated carboxylic acids is provided.

Enzymatic Aminolysis and Transamidation Reactions

Chiral amides can be obtained from (+/-)-2-chloropropionate esters and a wide range of amines when the reaction is catalyzed by Candida cylindracea lipase.The enantioselection of the enzyme in this aminolysis reaction depends on the substrate and nucleoph

A SIMPLE PROCEDURE FOR THE PREPARATION OF CHIRAL AMIDES

Yeast lipase (Candida cylindracea) catalysed the reaction between ethyl (+/-)-2-chloropropionate and different aliphatic and aromatic amines yielding optically active amides.

LEWIS ACID MEDIATED AMINOLYSIS OF ESTERS: CONVERSION OF METHYL (S)-(-)-2-CHLOROPROPIONATE TO (S)-(+)-N,N-DIETHYL-2-CHLOROPROPIONAMIDE

Methyl (S)-(-)-2-chloropropionate 1 is converted to (S)-(+)-N,N-diethyl-2-chloropropionamide 2 in high chemical and optical yield using a Lewis acid/diethylamine reagent.