An Unexpected Oxidative C-O Bond Formation: 11,17a-Dihydrobenzo[4,5]oxazolo[3,2-A]dinaphtho[2,1- C:1',2'-E]azepine

Abstract

Phosphoric acids bound to 3,3’-subsituted 1,1’-binaphthalene-2,2’-diol (BINOL) have found wide application as effective asymmetric catalysts. In this work, we describe our attempt to construct a new binaphthalene-based phosphoric acid <b>6</b>. We found that both the key precursor <b>2</b> and the desired product <b>6 </b>decay rapidly and quantitatively to a stable dihydrooxazole <b>3</b> via an O<sub>2</sub>-driven oxidative C-O bond formation.