Asymmetric induction in cyclohexadienones carrying α-d-glucopyranosyl moiety

Abstract Cyclohexadienone derivatives possessing α- d -glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C -glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.