Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

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• 作者：Fedor Romanov-Michailidis ; Marion Pupier ; C茅line Besnard ; Thomas B眉rgi ; Alexandre Alexakis
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：16
• 期：19
• 页码：4988-4991
• 全文大小：346K
• ISSN：1523-7052

文摘

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 <b>L3b>. Under optimized conditions, cyclopropylamines <b>Ab> were transformed into 尾-fluoro cyclobutylimines <b>Bb> 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 <b>Cb>, compounds of significant interest in the pharmacological industry.