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Diastereoselective Synthesis of Benzoxanthenones
Author(s) -
Neuhaus William C.,
Kozlowski Marisa C
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901727
Subject(s) - chemistry , diastereomer , vanadium , oxidizing agent , enantioselective synthesis , oxidative coupling of methane , catalysis , moiety , monomer , phenol , combinatorial chemistry , schiff base , oxidative phosphorylation , phenols , solvent , organic chemistry , polymer chemistry , polymer , biochemistry
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.