| Abstract
| - Addition of phenyllithium to a mixture of an imine, methylo-iodobenzoate, and BF3·etherateat−105 °C gives good to excellent yields of isoindolones. Thetransient formation of methylo-lithiobenzoate is proposed, which is formed by a rapidlithium/iodide exchange reaction of thephenyllithium with methyl o-iodobenzoate in the presence ofthe imine. The transiently generatedanions can then be captured by the BF3-activated imines toform the isoindolones in good to highyield. The reactions conditions are sufficiently mild, andselective, to permit functional groupssuch carbmethoxy and aryl bromide, which could otherwise react with theadded PhLi, to betolerated.
|
