Our research group has been maintaining a longstanding interest in the synthesis of tetrahydropyran-containing natural products.The base and acid catalyzed intramolecular <i>oxa</i>-Michael cyclisation proved to be a widely applicable method for the stereoselective construction of the tetrahydropyran moiety with various substitution patterns. Despite the more than fifty precedents of this transformation in the literature, there has been no clear elucidation of the origin of stereocontrol. Hence, the purpose of the present study is to provide a reasonable explanation for the observed selectivity based on the results of our intensive experimental and computational investigations.

Combined DFT and experimental study of the base and acid catalyzed <i>oxa</i>-Michael reaction in THP synthesis: Reinterpretation of the selectivity-determining factors

255th National Meeting (2018)

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Combined DFT and experimental study of the base and acid catalyzed oxa-Michael reaction in THP synthesis: Reinterpretation of the selectivity-determining factors