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Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

Published in Organic letters. 2014, vol. 16, no. 19, p. 4988-4991
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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ROMANOV MICHAILIDIS, Fedor et al. Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement. In: Organic letters, 2014, vol. 16, n° 19, p. 4988-4991. doi: 10.1021/ol5022355 https://archive-ouverte.unige.ch/unige:41312

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Deposited on : 2014-10-29

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