The temperature dependence of the diastereoselective reduction of 2-t-butylcyclohexanone with diisobutyl-aluminium-2,6-di-t-butyl-4-methylphenoxide

Article abstract of DOI:10.1016/S0040-4020(01)81335-1

The diastereoselectivity of the reduction of 2-t-butylcyclohexanone (1) with diisobutylaluminium-2,6-di-t-butyl-4-methylphenoxide (2) is investigated as a function of the temperature and the conversion. The relevant selection steps are characterized on the basis of the isoinversion principle. The kinetically controlled formation of the alcoholate intermediates as well as the thermodynamically controlled Meerwein-Ponndorf-Verley type equilibration are recognized as the two selection steps of the reduction.