Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2H-azepin-2-one

β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2H-azepin-2-one
David J. Aitken, Juan Xie, Sylvie Robin, François Brisset, Ogaritte Yazbeck, Julien Buendia, Daoud Naoufal, Ali T. Mansour
The photochemical electrocyclization reaction of the title compound in the presence of β-cyclodextrin was examined in different conditions. No enantioselectivity was observed in solution, but solid-state reactions of a 1:1 complex as a suspension or a thin film, followed by reduction, provided (1R,5R)-2-azabicyclo[3.2.0]heptan-3-one in isolated yields up to 79% and with ee values up to 45%.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01300

DOI: 10.1021/acs.joc.7b01300

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