337. F. Romanov-Michailidis, M. Pupier, C. Besnard, T. Bürgi, A. Alexakis,
     “Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement”
     Org. Lett. 2014, 16, 4988-4991.

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 into β-fluoro cyclobutylimines B in good yields and high levels of diastereo- and enantiocontrol. 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.

DOI : 10.1021/ol5022355 

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