First example of 'diastereotopic face activation' and chiral recognition without metal assistance. A novel 5-deazaflavin enzyme model

Article abstract of DOI:10.1016/S0040-4039(00)60865-1

A chiral 5-deazaflavin 1 with 2-hydroxynaphthyl group at N(3) position of the pyrimidine ring moiety was synthesized. 1 underwent, in the absence of magnesium ion, a '(net) hydride transfer' from BNAH to C(5) almost exclusively on the face where OH group