124097-40-1

Upstream product

• 13704-09-1 (S)-(-)-ethyl mandelate 
• 17199-29-0 (S)-Mandelic acid 
• 21210-43-5 (S)-Methyl mandelate 

Downstream Products

• 207516-06-1 (S)-N-((1R,4S,5R)-5-Benzyloxymethyl-4-hydroxy-cyclopent-2-enyl)-2-hydroxy-2-phenyl-acetamide 
• 1415265-23-4 (1R,4S,αR)-3-(α-hydroxyphenylacetyl)-2-oxa-3-aza-bicyclo[2,2,1]hept-5-ene 
• 126924-22-9 (1S,4R,αR-)-3-(α-hydroxyphenylacetyl)-2-oxa-3-aza-bicyclo[2,2,1]hept-5-ene 
• 121129-43-9 Acetic acid (S)-2-(1R,4S)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-en-3-yl-2-oxo-1-phenyl-ethyl ester 
• 121129-43-9 Acetic acid (S)-2-(1S,4R)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-en-3-yl-2-oxo-1-phenyl-ethyl ester 
• 207516-21-0 Acetic acid (1R,2S,3S,4S,5R)-2,3,4-triacetoxy-1-acetoxymethyl-5-phenylacetylamino-cyclopentyl ester 
• 207516-74-3 Acetic acid (1R,2S,3R,4S,5R)-2,3,4-triacetoxy-1-acetoxymethyl-5-phenylacetylamino-cyclopentyl ester 
• 1053255-18-7 Acetic acid (1S,2R,3R,4S,5R)-4,5-diacetoxy-2-hydroxy-2-hydroxymethyl-3-phenylacetylamino-cyclopentyl ester 
• 207516-72-1 Acetic acid (1S,2S,3R,4R,5S)-2,3-diacetoxy-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester 
• 207516-15-2 Acetic acid (1S,2R,3R,4R,5S)-2,3-diacetoxy-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester 
• 207516-73-2 Acetic acid (1S,2S,3R,5S)-2,3-diacetoxy-4-methylene-5-phenylacetylamino-cyclopentyl ester 
• 207516-17-4 Acetic acid (1S,2R,3R,5S)-2,3-diacetoxy-4-methylene-5-phenylacetylamino-cyclopentyl ester 
• 207516-40-3 Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-5-((S)-2-acetoxy-2-phenyl-acetylamino)-4-benzyloxymethyl-2-bromo-cyclopentyl ester 
• 207516-49-2 Acetic acid (1R,2R,3R,4S,5R)-2,4-diacetoxy-1-acetoxymethyl-3-bromo-5-phenylacetylamino-cyclopentyl ester 

Relevant academic research and scientific papers

Controlled racemization and asymmetric transformation of α-substituted carboxylic acids in the melt

The racemization and asymmetric transformation of a series of α- substituted carboxylic acids, viz. mandelic acid, hydratropic acid, ibuprofen and naproxen, were studied. Several racemization methods for mandelic acid were studied and it was found that base-catalyzed racemization in aprotic polar solvents was the most efficient method. Moreover, a fast and mild base- catalyzed racemization reaction in the melt was developed. DBN turned out to be a very efficient racemizing base for the substrates studied. Combination of the base-catalyzed racemization in the melt with known resolution processes resulted in crystallization-induced asymmetric transformations. Treating racemic ibuprofen or hydratropic acid with 1.5-2.5 equivalents of enantiopure α-methylbenzylamine and a catalytic amount of DBN resulted in the isolation of enantiomerically enriched ibuprofen or hydratropic acid with ees of up to 75% and almost quantitative yields.

Asymmetric Induction in the Diels-Alder Reactions of α-Hydroxy Acyl Nitrones

The hydroxamic acids 7, derived from a series of α-hydroxy acids 5, have been oxidised with periodate to form transient, chiral acyl nitroso compounds 8, which were trapped in situ with cyclopentadiene and cyclohex-1,3-diene to give mixtures of diastereoi

ASYMMETRIC INDUCTION IN THE DIELS-ALDER REACTIONS OF α-HYDROXYACYLNITROSO COMPOUNDS

Transient, chiral α-hydroxyacylnitroso compounds (2), able to form intramolecular hydrogen bonds, react stereoselectively with cyclopentadiene and cyclohexa-1,3-diene; the cycloadduct (6) of the latter diene and the nitroso derivative of (S)-mandelic acid