Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives

Attachment of chiral auxiliaries to 2-benzoyladamantane-2-carboxylic acid, either covalently through ester formation with optically pure alcohols, or ionically via salt formation with optically pure amines, leads to substrates whose irradiation in the crystalline state affords chiral rearranged photoproducts in ≥96% diastereo- and enantiomeric excess.