Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones
Qiao Yan, Martin G. Banwell, Paul D. Carr, Yuhua Bai, Anthony C. Willis, Benoit Bolte
A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels–Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01243

DOI: 10.1021/acs.joc.7b01243

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