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

06 May 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 6. We found that both the key precursor 2 and the desired product 6 decay rapidly and quantitatively to a stable dihydrooxazole 3 via an O2-driven oxidative C-O bond formation.

Keywords

axial chirality
binaphthol
azepine
Bronsted Acids
C-O bond formation
oxidation
dihydrooxazole

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