Synthesis of 6,7-benzo-3-borabicyclo[3.3.1]nonane and its 3-aza analog from 2-allylphenyl(diallyl)borane.Intramolecular arylboration of the C=C bond

摘要

A method was developed for the synthesis of 6,7-benzo-3-borabicyclo[3.3.1]nonane and 6,7-benzo-3-azabicyclo[3.3.1]nonane derivatives based on intramolecular cyclization of 2-allylphenyl(diallyl)borane.Intramolecular arylboration of the double bond in 1,5-diallyl-2,3-benzo-l-boracyclohexane was carried out for the first time.Conventional oxidation (H_2O_2-OH~-) of 6,7-benzo-3-methoxy-3-borabicyclo[3.3.1]nonane afforded cis-l,3-di(hydroxymethyl)tetralin.The structure of the latter was established by X-ray diffraction analysis.