Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of alpha-chloroesters.
Treatment of alpha,alpha-dichloroaldehydes with various phenols in the presence of chiral triazolium salt catalysts and excess base results in the synthesis of alpha-chloro aryl esters in good yield and enantioselectivity. The reaction is tolerant of various functionality on the aldehyde as well as several electronically diverse phenols. The product chloroesters were further transformed into chloroacid, chlorohydrin, and azidoesters with nearly complete retention of enantioselectivity.
Reynolds
Nathan T
NT
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Rovis
Tomislav
T
D002384:Catalysis; D002713:Chlorine / Q000737:chemistry* / Q000378:metabolism; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D011522:Protons; D013237:Stereoisomerism
D004952:Esters; D011522:Protons; D002713:Chlorine