Work

Selective Oxidation of 8,8′-Hydroxylated Binaphthols to Bis-spironaphthalenones or Binaphtho-para- and Binaphtho-ortho-quinones

Year: 2012

Type: article

Abstract: The selective oxidation of a series of functionalized 8,8'-hydroxylated binaphthols to binaphtho-para- and binaphtho-ortho-quinones has been realized using either a Co-salen catalyst or ortho-iodoxybenzoic acid. A unique spirocyclic bis-spironaphthalenone was also obtained in good yield via a phenyliodonium diacetate promoted oxidative dearomatization.

Source: Organic Letters

DOI: 10.1021/ol302195e

Authors: Erin E. Podlesny, Patrick J. Carroll, Marisa C. Kozlowski

Institution: University of Pennsylvania

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institute of General Medical Sciences, National Center for Research Resources, Division of Chemistry

Awards: Time-Of-Flight Instrument with Variable Ionization Sources, Synthesis of Bisanthraquinone Natural Product and BINOL-type Chiral Ligands, NMR systems : 2 Bruker Avance 500 Consoles, Predoctoral Training at the Chemistry-Biology Interface