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

Mansour, AT; Buendia, J; Xie, J; Brisset, F; Robin, S; Naoufal, D; Yazbeck, O; Aitken, DJ, Journal of Organic Chemistry, 2017, 82, 9832-9836.

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%.

Type :

Publication

Dates :

Paru le 15 septembre 2017

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DOI: 10.1021/acs.joc.7b01300