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

J Org Chem. 2017 Sep 15;82(18):9832-9836. doi: 10.1021/acs.joc.7b01300. Epub 2017 Sep 1.

Abstract

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%.

Publication types

  • Research Support, Non-U.S. Gov't