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

preprint
submitted on 04.05.2020 and posted on 06.05.2020 by Michael Abraham, Philipp Honegger
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.

History

Email Address of Submitting Author

philipp.honegger@univie.ac.at

Institution

University of Vienna

Country

Austria

ORCID For Submitting Author

0000-0001-8225-671X

Declaration of Conflict of Interest

no conflict of interest

Version Notes

Initial version

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