α-Azido ketones, Part 6. Reduction of acyclic and cyclic α-azido ketones into α-amino ketones: old problems and new solutions

Abstract

Comparative experiments on the selective reduction of -azido ketones to -amino ketones revealed that tin(II) chloride reduction followed by immediate protection with Boc group is the method of choice. This methodology proved to be useful for more complex substrates, too. Chromium(II) acetate also resulted in the desired products but in lower yields due to a competitive deazidation procedure. A mechanism to explain this deazidation was suggested.