Lipophilic oligopeptides for chemo-and enantioselective acyl transfer reactions onto alcohols

…, D Zell, R Hrdina, RC Wende, L Wanka…

Index: Mueller, Christian E.; Zell, Daniela; Hrdina, Radim; Wende, Raffael C.; Wanka, Lukas; Schuler, Soeren M. M.; Schreiner, Peter R. Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8465 - 8484

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Citation Number: 18

Abstract

Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac-and meso-cycloalkane-1, 2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full ...

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