88825-14-3

Upstream product

• 88820-80-8 N-(6-Deoxy-1,2;3,4-di-O-cyclohexyliden-α-D-galactopyranosyliden)alanin-methylester 
• 4392-24-9 Cinnamyl bromide 
• 78354-69-5 (S)-2-Isopropyl-3,6-dimethoxy-5-((E)-3-phenyl-allyl)-2,5-dihydro-pyrazine 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 81177-58-4 (2S,5S)-5-Isopropyl-3,6-dimethoxy-2-methyl-2-((E)-3-phenyl-allyl)-2,5-dihydro-pyrazine 

Relevant academic research and scientific papers

A practical asymmetric synthesis of α-methyl α-amino acids using a chiral cu-salen complex as a phase transfer catalyst

The asymmetric C-alkylation of N-benzylidene alanine methyl ester has been achieved using a copper(II) (salen) complex as an asymmetric phase transfer catalyst and provides a practical synthesis of α-methyl α-amino acids with up to 86% enantiomeric excess. (C) 2000 Elsevier Science Ltd.

Asymmetric Syntheses via Heterocyclic Intermediates, V. - Asymmetric Synthesis of α-Methyl Amino Acids by Alkylation of the Lithiated Lactim Ether of cyclo-(L-Ala-L-Ala)

The (3S,6S)-2,5-dimethoxy-3,6-dimethyl-3,6-dihydropyrazine (7) is obtained from cyclo-(L-Ala-L-Ala) 5 (93-95percent optically pure) and trimethyloxonium tetrafluoroborate.With butyllithium the lithio derivative 8 is formed which reacts with alkyl halides in good chemical yields and with more than 90percent diastereoselectivity, whereby R-configuration is induced at C-3.A model concept is discussed, which explains the remarkably high asymmetric induction. - Hydrolysis (0.25 N HCl, room temp.) gives L-alanine methyl ester (4) and the (R)-α-methyl amino acid methyl esters 13.The two amino acid esters are separable by distillation or chromatography.