Studies on diastereoselective reduction of cyclic β-ketoesters with boron hydrides. Part 4: The reductive profile of functionalized cyclohexanone derivatives

Reduction of 2-allyl-2-carboalkoxycyclohexanones (), 2-propyl-2-carboethoxycyclohexanone () and 2-benzyl-2-carboethoxycyclohexanone () with boron hydrides in the presence and absence of several chelating agents were studied. Molecular modeling studies using semiempirical PM3 method were performed in order to find a suitable explanation of the diastereoselection of ketone carbonyl faces during the reductive process, which yielded trans-2-allyl-2-carboethoxycyclohexanol () and cis-2-allyl-2-carboethoxycyclohexanol () in good diastereomeric excess by using inexpensive sodium and tetrabutylammonium borohydrides.