Pseudomonas fluorescens lipase-catalyzed asymmetric hydrolysis and transesterification of meso-2,5-bis(acetoxymethyl)- and bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran

Add time:07/28/2019    Source:sciencedirect.com

Pseudomonas fluorescens lipase (PFL)-catalyzed asymmetric hydrolysis of meso-2,5-bis(acetoxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 3 afforded the optically active monoacetate (−)-7 of high enantiomeric excess (92% ee) in 94% yield. Transesterification of meso-bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran6 using PFL in vinyl acetate gave the monoacetate (+)-7 of 69% ee in low yield (15%). The absolute configuration of (−)-7 was determined to be 2S,3S,4R,5R, by chemical correlation with d-allose 10.

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