Solvation effects on stereochemistry of reduction of 3,3,5-trimethylcyclohexanone with lithium aluminum tri-t-butoxyhydride

Article abstract of DOI:10.1016/0040-4020(78)88370-7

Specific solvation effects on stereoselectivity in the reduction of a cyclohexanone by lithium aluminum tri-t-butoxyhydride have been studied by adding measured quantities of diethyl ether, tetrahydrofuran (THF) and methyl-substituted tetrahydrofurans to benzene solvent, and various amounts of THF to diethyl ether solvent. A steric hindrance effect in the case of bulky addends was observed, and a significant increase in stereoselectivity for less bulky addends was found. The results have been explained in terms of complexing, or steric hindrance to complexing, of the lithium cation.