Diastereoselective Synthesis of trans-ß-Amino Cyclohexyl Ketones and trans-3-Amino-4-acyl-tetrahydropyrans from Intramolecular C-Alkylation of ω-Halo-Substituted ß-Sulfinamido Ketones.

Reaction of ω-halo-substituted nonracemic ß-sulfinamido ketones with NaH afforded the ß-amino cyclohexyl ketones in excellent yields and diastereoselectivity, via an intramolecular C-alkylation, α to the carbonyl group. The reaction was found to be general and can be applied for the synthesis of different cyclohexyl amino ketones and tetrahydropyrans possessing amine and acyl substitutions.