Tetrahedron

Selective enzymatic transformations of itaconic acid derivatives: an access to potentially useful building blocks

P Ferraboschi, S Casati, P Grisenti, E Santaniello

Index: Ferraboschi, Patrizia; Casati, Silvana; Grisenti, Paride; Santaniello, Enzo Tetrahedron, 1994 , vol. 50, # 10 p. 3251 - 3258

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Citation Number: 25

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 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 ...