Kinetic Resolution of 2‑Aryl-4-methylenepiperidines toward Enantioenriched Functionalizable Piperidine Fragments

• Published in: Journal of organic chemistry Vol. 87; no. 13; pp. 8819 - 8823
• Main Authors: Choi, Anthony, Meijer, Anthony J. H. M., Silvestri, Ilaria Proietti, Coldham, Iain
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.2022; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; LITHIATION; INHIBITOR; DERIVATIVES; DISCOVERY

The base n-BuLi with sparteine allows a kinetic resolution of N-Boc-2-aryl-4-methylenepiperidines. The 2,2-disubstituted products and recovered starting materials were isolated with high enantiomeric ratios. From VT-NMR spectroscopy and DFT studies, the rate of rotation of the N-Boc group is fast. L...