Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

An efficient and highly stereoselective fluorinative aza-semipinacol rearrangement is described. The catalytic reaction requires use of Selectfluor in combination with the chiral enantiopure phosphate anion derived from acid L3 Under optimized conditions, cyclopropylamines A were transformed in to beta-Fluoro cyclobutylimnes B in good yields and high levels of diastero and enatiocontrol Furthermore the optically active cyclobutylimines were reduced diastereoselectively with L-Selectride in the corresponding fluorinated amines C, compounds of significant interest in the pharmacological industry.