Hydrolytic enzymes regioselectively catalyze the hydrolysis of diethyl itaconate 5a to the monoester 5c and opening of itaconic anhydride 6 to the regioisomeric monoester 5b that was tranformed into the hydroxy esters 2. This was used for the synthesis of beta-methylene-gamma-butyrolactone 7 and of the racemic epoxyalcohol 3, that was resolved by a highly enantioselective Pseudomonas fluorescens lipase-catalyzed transesterification into (S)-3 and (S)-8 (90 and 86% ee, respectively).
SELECTIVE ENZYMATIC TRANSFORMATIONS OF ITACONIC ACID-DERIVATIVES - AN ACCESS TO POTENTIALLY USEFUL BUILDING-BLOCKS / P. FERRABOSCHI, S. CASATI, P. GRISENTI, E. SANTANIELLO. - In: TETRAHEDRON. - ISSN 0040-4020. - 50:10(1994), pp. 3251-3258. [10.1016/S0040-4020(01)81120-0]
SELECTIVE ENZYMATIC TRANSFORMATIONS OF ITACONIC ACID-DERIVATIVES - AN ACCESS TO POTENTIALLY USEFUL BUILDING-BLOCKS
P. FerraboschiPrimo
;S. CasatiSecondo
;E. SantanielloUltimo
1994
Abstract
Hydrolytic enzymes regioselectively catalyze the hydrolysis of diethyl itaconate 5a to the monoester 5c and opening of itaconic anhydride 6 to the regioisomeric monoester 5b that was tranformed into the hydroxy esters 2. This was used for the synthesis of beta-methylene-gamma-butyrolactone 7 and of the racemic epoxyalcohol 3, that was resolved by a highly enantioselective Pseudomonas fluorescens lipase-catalyzed transesterification into (S)-3 and (S)-8 (90 and 86% ee, respectively).
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