The Attractive Application of Lactol Chemistry: From Racemic Lactol to Natural Product Skeleton

Abstract

A versatile methodology involving the use of substituted racemic lactols as nucleophiles in the enamine-based asymmetric reactions leading to functionalized lactones with multiple stereogenic centers as one single diastereoisomer is reported. Importantly, the desired products could be easily transformed into asymmetric 2,4,5-trisubstituted piperidine derivatives, which are present in numerous alkaloid products but difficult to prepare optically enriched. Moreover, although starting from racemic precursors, the stereoisomeric products were discretely provided by simple column chromatography, which could meet the requirements of atom economy and efficiency.

Key words

alkaloids - asymmetric catalysis - heterocycles - lactones - Michael­ addition - piperidines

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