Lipase-Catalyzed Second-Order Asymmetric Transformations as Resolution and Synthesis Strategies for Chiral 5-(Acyloxy)-2(5H)-furanone and Pyrrolinone Synthons

Abstract

Link to publication in University of Groningen/UMCG research database Citation for published version (APA): vanderDeen, H., Cuiper, A. D., Hof, R. P., vanOeveren, A., Feringa, B. L., & Kellogg, R. M. (1996). Lipasecatalyzed second-order asymmetric transformations as resolution and synthesis strategies for chiral 5-(acyloxy)-2(5H)-furanone and pyrrolinone synthons.

Approaches based on enzyme mediated kinetic to dynamic kinetic resolutions: A versatile route for chiral intermediates

“…5-(Acyloxy)-2-(5H)-furanones1 and pyrrrolidines 2 have been synthesized in enantiomerically pure form by exploiting the property of spontaneous in situ racemization leading to complete resolution by coupling the kinetic resolution to an asymmetric transformation [159] (second order asymmetric transformation). Racemization occurs spontaneously under the reaction conditions (Scheme 75).…”

Dynamic covalent chemistry in enzyme catalysis

“…Figure 5 Applications of hemiacetal formation reaction in dynamic kinetic resolution [31][32][33] 图 6 半胺醛反应(A) [35] 及硫代半缩醛反应(B, C) [26,37] 在动 态动力学拆分中的应用举例 Figure 6 Applications of (A) [35] hemiaminal and (B, C) [26,37] hemithioacetal formation reactions in dynamic kinetic resolution 图 7 氰醛反应(A) [40] 及硝基羟醛反应(B) [42] 在动态动力学 拆分中的应用举例 Figure 7 Applications of (A) [40] cyanohydrin and (B) [42] nitroaldol reactions in dynamic kinetic resolution 图 8 在动态动力学拆分中常用的亚胺加成反应…”

Synthesis of Chirally Pure Enantiomers by Lipase

“…Lipases are frequently used as an asymmetric catalyst for the preparation of enantiomerically pure organic compounds 62 .…”