90581-53-6

Upstream product

• 100-52-7 benzaldehyde 
• 611-71-2 MANDELIC ACID 
• 56535-98-9 2,5-diphenyl-[1,3]dioxolan-4-one 
• 17199-29-0 (S)-Mandelic acid 

Downstream Products

• 64471-45-0 (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid 
• 64471-43-8 (S)-α-cyclopentyl-α-hydroxy-α-phenylacetic acid 
• 860469-61-0 (S)-N-trichloroethoxyformyl-3-azabicyclo[3,3,1]nonan-9-yl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate 
• 230632-95-8 (S)-N-methyl-3-azabicyclo[3,3,1]nonan-9-yl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate 
• 230313-75-4 (R)-N-methyl-3-azabicyclo[3,3,1]nonan-9-yl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate 
• 64471-47-2 (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester 
• 860644-54-8 (S)-methyl-α-cyclopentyl-α-hydroxyl-α-phenylacetate 

Relevant academic research and scientific papers

Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones

An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed.

Optical resolution, stereoselective synthesis, and crystal structure of 9α-(3-azabicyclo[3,3,1]nonanyl)-2′cyclopentyl-2′-hydroxy- 2′-phenylacetate

9α-(3-Azabicyclo[3,3,1 ]nonanyl)-2′-cyclopentyl-2′- hydroxy-2′-phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N-p-toluenesulfonylglutamic acid. Optical pure 1 was also effect

α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS

α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-1,3-dioxolanones or 1,3-oxathiolanones (2); the predominate cis-isomers are separeted by crystallization.The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid funish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones, and hydrolysis α-branched α-hydroxy-carboxylic acids (3, 6, 8, 9, 10).These result from an overall substitution of the proton in the α-CO position with retention of configuration.The optically active carboxylic acids are α-alkylated without racemization and without employment of a chiral auxiliary ("self-reproduction of chirality", Scheme 1).The diastereoselectivities (ds) are generally >95percent (Table 1, 2, and 20-25).

Flash Vacuum Thermolysis of 1,3-Dioxolan-4-ones

Flash vacuum thermolysis of 1,3-dioxolane-4-ones yields aldehydes and ketones as the major products as the result of apparent decarboxylation of α lactones formed by collapse of a 1,3 dipole.When phenyl substituents are present, epoxides are also formed via the intermediacy of a carbonyl ylide.