Role of the heteroatoms in the complex metal hydride reduction of 2-t- butyl-1,3-dioxan-5-one and 3-oxoquinolizidine: Comparison of their reactivity and stereochemistry with those of the corresponding carbocyclic compounds

Article abstract of DOI:10.1246/bcsj.72.285

The complex metal hydride reductions of 2-t-butyl-1,3-dioxan-5-one (1) and 3-oxoquinolizidine (3) are faster than those of the corresponding carbocyclic compounds, 4-t-butylcyclohexanone (2) and trans-2-decalone (4). The stereoselectivities were similar in the LiAlH₄ reduction, but the heteracyclohexanones exhibited higher stereoselectivity with NaBH₄. These facts are discussed in terms of the intramolecular orbital interaction.