Tetrahedron: Asymmetry

Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal acetals

G Egri, E Fogassy, L Novák, L Poppe

Index: Egri, Gabriella; Fogassy, Elemer; Novak, Lajos; Poppe, Laszlo Tetrahedron Asymmetry, 1997 , vol. 8, # 4 p. 547 - 557

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Citation Number: 14

Abstract

Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one-or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes ...