Switching from S-to R-selectivity in the Candida antarctica lipase B-catalyzed ring-opening of ω-methylated lactones: Tuning polymerizations by ring size

…, L Roumen, JAJM Vekemans, K Pieterse…

Index: Van Buijtenen, Jeroen; Van As, Bart A. C.; Verbruggen, Marloes; Roumen, Luc; Vekemans, Jef A. J. M.; Pieterse, Koen; Hilbers, Peter A. J.; Hulshof, Lumbertus A.; Palmans, Anja R. A.; Meijer Journal of the American Chemical Society, 2007 , vol. 129, # 23 p. 7393 - 7398

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Citation Number: 52

Abstract

Novozym 435-catalyzed ring-opening of a range of ω-methylated lactones demonstrates fascinating differences in rate of reaction and enantioselectivity. A switch from S-to R- selectivity was observed upon going from small (ring sizes≤ 7) to large lactones (ring sizes≥ 8). This was attributed to the transition from a cisoid to a transoid conformational preference of the ester bond on going from small to large lactones. The S-selectivity of the ...