An Expeditious Route to Monoprotected α-Keto Aldehydes with Control of Regiochemistry

Abstract

Treatment of representative orthoesters (2) with pyruvonitrile (3) afforded the corresponding α, α-diethoxynitriles (4) in 65–80% yields. Subsequent reduction of the latter using lithium aluminum hydride, followed by careful hydrolysis of the aldimine intermediates, led to the procurement of α, α-dialkoxy aldehydes (5) in 80–90% yield.