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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Enantioselective catalytic fluorinative aza-semipinacol rearrangement
Fedor Romanov-Michailidis1, Marion Pupier, Céline Besnard
1Department of Organic Chemistry, ‡Laboratory of Crystallography, and §Department of Physical Chemistry, University of Geneva , Quai Ernest Ansermet 30 CH-1211 Geneva 4, Switzerland.
Abstract:
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.
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