Hill Jarvis, Tam William
Department of Chemistry , University of Guelph , Guelph , Ontario , Canada , N1G 2W1.
J Org Chem. 2019 Jun 21;84(12):8309-8314. doi: 10.1021/acs.joc.9b01094. Epub 2019 Jun 13.
The palladium/Lewis acid cocatalyzed ring-opening reaction of various C-substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C regioisomeric ring-opened products has been proposed.
研究了钯/路易斯酸共催化各种碳取代的不对称氧杂苯并降冰片二烯（OBD）与肟亲核试剂的开环反应。探索了各种碳取代基的影响。对于吸电子基团，获得了中等至优异的产率和优异的区域选择性。供电子烷基的存在导致相应的OBD异构化，从而得到取代的萘酚衍生物。此外，还提出了形成碳区域异构体开环产物的机理。
