Asymmetric Hydrolysis of (±)-α-Substituted Garboxylic Acid Esters with Microorganisms

Abstract

Microorganisms that hydrolyze methyl2-phenylpropionate (1) or reduce 4-phenyl-2-butanone (3) were screened from 250 type cultures. Several Aspergilli and two bacteria hydrolyzed ester 1, and Asp. sojae lAM 2703 preferentially hydrolyzed (R)-isomer of (±)-1, whereas Bacillus subtilis var. niger lFO 3108 and Mycobacterium smegma tis ATCC 10143 preferentially hydrolyzed (S)-isomer. The hydrolysis of the related esters of 1 with these organisms was also examined.

Dynamic Enzymatic Kinetic Resolution of Methyl 2,3‐Dihydro‐1H‐indene‐1‐carboxylate

“…Furthermore, the acid has been successfully employed as a chiral derivatisation agent in NMR spectroscopy after fluorination in the α position, yielding higher Δ δ F values than the conventional MTPA esters 13. Despite the simple structure and the common occurrence of the substructure of acid 1 , only a few approaches to enantiopure indane‐1 H ‐carboxylic acid and its derivatives, utilizing either whole‐cell biotransformation14 or fractional crystallisation,15,16 had been reported, but either the enantiomeric excess ( ee ) was not satisfactory or the procedures were quite extensive. An efficient DKR procedure would greatly facilitate access to the title compound.…”