Generation and Reactions of Lithiated tert-Butyl and 2,6-Di(tert-butyl)-4-methylphenyl Cyclopropanecarboxylates

tert-Butyl and 2,6-di(tert-butyl)-4-methylphenyl (BHT) cyclopropanecarboxylates ( 4 , 6 , 24 , 25 ) are lithiated with LiN(i-Pr)₂ and t-BuLi, respectively. Reactions with alkyl halides, aldehydes, acyl chlorides, and heteroelectrophiles give α-substituted BHT esters which can be cleaved (t-BuOK/H₂O/THF) to the corresponding carboxylic acids or reduced (LiAlH₄/THF) to the cyclopropanemethanols.