Romanov-Michailidis Fedor, Pupier Marion, Besnard Céline, Bürgi Thomas, Alexakis Alexandre
Department of Organic Chemistry, ‡Laboratory of Crystallography, and §Department of Physical Chemistry, University of Geneva , Quai Ernest Ansermet 30 CH-1211 Geneva 4, Switzerland.
Org Lett. 2014 Oct 3;16(19):4988-91. doi: 10.1021/ol5022355. Epub 2014 Sep 12.
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.
描述了一种高效且高度立体选择性的氟化氮杂半频哪醇重排反应。该催化反应需要使用Selectfluor与由酸L3衍生的手性、对映体纯的磷酸根阴离子相结合。在优化条件下，环丙胺A以良好的产率和高水平的非对映和对映选择性转化为β-氟环丁基亚胺B。此外，光学活性的环丁基亚胺在相应的氟化胺C中用L-Selectride进行非对映选择性还原，氟化胺C是制药行业中具有重要意义的化合物。
