Application of Regio- and Stereoselective Functional Group Transformations of Chiral Aziridine-2-carboxylates

초록

Chiral aziridine-2-carboxylates have two important functional groups, the carboxylate group and aziridine ring, that are useful for synthetic purposes. As both (2R)- and (2S)-aziridine-2-carboxylates were commercialized in optically pure forms, we have studied to extend their synthetic utilities for the construction of various nitrogen-containing molecules. The C2 ester group can be transformed into aldehydes, alcohols, amides, ketones, beta-ketoesters, and amines bearing diverse substituents with defined stereochemistry in high yields. In particular, ring-opening reactions of aziridines are carried out in regio- and stereoselective manners toward alpha- or beta-amino cyclic and acyclic compounds in optically pure forms. The highlight of this chemistry based on the regio- and stereoselective functional-group transformations of aziridine-2-carboxylates is exemplified by efficient and highly stereoselective syntheses of many biologically important amines, including natural products.

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