Diastereoselective Synthesis of Benzoxanthenones

8Citations
Citations of this article
7Readers
Mendeley users who have this article in their library.
Get full text

Abstract

An oxidative catalytic vanadium(V) system was developed to access the naturally nonabundant diastereomers of carpanone from the corresponding alkenyl phenol monomer in one pot by tandem oxidation, oxidative coupling, and 4+2 cyclization. This system was applied to the synthesis of two other analogues of carpanone. Mild oxidizing silver salts were used as the terminal oxidant to minimize background oxidation which produces the natural diastereomer of carpanone. Further, the first examples of enantioselective oxidative benzoxanthenone formation are reported. Solvent polarity has a strong effect on enantioselectivity, consistent with a mechanism involving binding of vanadium Schiff base catalysts to the alcoholic moiety of the alkenyl phenols during the cyclization step.

Cite

CITATION STYLE

APA

Neuhaus, W. C., & Kozlowski, M. C. (2020). Diastereoselective Synthesis of Benzoxanthenones. Chemistry - An Asian Journal, 15(7), 1039–1043. https://doi.org/10.1002/asia.201901727

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free