151123-29-4

Upstream product

• 1013-88-3 Benzophenone imine 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 171181-53-6 methyl N^α-(diphenylmethylene)-DL-phenylglycinate 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 

Downstream Products

• 138892-13-4 (R)-(Benzhydrylidene-amino)-phenyl-acetic acid isopropyl ester 
• 133545-89-8 [(1R)-2-(benzyloxy)-2-oxo-1-phenylethyl]ammonium 4-methyl-1-benzensulfonate 
• 875-74-1 (R)-phenylglycine 
• 138892-12-3 (R)-(Benzhydrylidene-amino)-phenyl-acetic acid benzyl ester 

Relevant academic research and scientific papers

A convenient method for the enantiomeric separation of α-amino acid esters as benzophenone imine schiff base derivatives

A convenient liquid chromatographic method for the separation of α-amino acid esters as benzophenone Schiff base derivatives on coated chiral stationary phases (CSPs) (Chiralcel OD-H, Chiralcel OD, Chiralpak AD-H, Chiralpak AD, and Chiralpak AS) or covalently immobilized CSPs (Chiralpak IA, Chiralpak IB, and Chiralpak IC) derived from polysaccharide derivatives is described. Benzophenone imine derivatives of α-amino acid esters were readily prepared by stirring benzophenone imine and the hydrochloride salts of α-amino acid esters in 2-propanol. The chromatographic separations were conducted at a flow rate 1.0 mL/min and a detection wavelength of 254 nm; 0.5% 2-propanol/hexane (v/v) was used on CSPs. In general, the resolution of Chiralpak IC was superior to those of the other CSPs. In addition, the resolutions of other arylimine derivatives of α-amino acid esters and the effects of different mobile phases on the enantiomeric separation of α-amino acid esters as benzophenone imine derivatives on Chiralpak IC were investigated.

Investigation into the enantioselective protonation of enolate Schiff bases with (R)-pantolactone

The effect of several factors on the enantioselective protonation of the enolates of α-amino acid derivatives with (R)-pantolactone were studied. The highest stereoselectivity (74-76% e.e.) was generally observed by associating lithium chloride with LHMDS

Oxygen alkylation of Schiff base derivatives of amino acids

Higher imine esters 1a-h and 7a-b of amino acids and dipeptides are prepared in 68-91% yield by saponification of the benzophenone Schiff base methyl esters 3a-d and 6 using phase-transfer techniques followed by O-alkylation with an alkyl halide. The procedure occurs with retention of configuration at the α-carbon except with phenylglycine derivatives.