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

Reaction of.-halo-substituted nonracemic beta-sulfinamido ketones with NaH afforded the beta-amino cyclohexyl ketones in excellent yields and diastereoselectivity, via an intramolecular C-alkylation, a 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.

Automated summary

Reaction of -halo-substituted nonracemic beta-sulfinamido ketones with NaH affords beta-amino cyclohexyl ketones in excellent yields and diastereoselectivity via intramolecular C-alkylation adjacent to the carbonyl group. This reaction is general and can be used for the synthesis of various cyclohexyl amino ketones and tetrahydropyrans with amine and acyl substitutions.