Tetrahedron p. 3251 - 3258 (1994)
Update date:2022-07-30
Topics:
Ferraboschi, Patrizia
Casati, Silvana
Grisenti, Paride
Santaniello, Enzo
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 transformed into the hydroxy esters 2. This was used for the synthesis of β-methylene-γ-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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