Choi, A., Meijer, A.J.H.M. orcid.org/0000-0003-4803-3488, Silvestri, I.P. et al. (1 more author) (2022) Kinetic resolution of 2-Aryl-4-methylenepiperidines toward enantioenriched functionalizable piperidine fragments. The Journal of Organic Chemistry, 87 (13). pp. 8819-8823. ISSN 0022-3263
Abstract
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. Lithiation and trapping of the enantioenriched starting materials gave 2,2-disubstituted piperidines with retention of stereochemistry. Functionalization of the 4-methylene group led to a variety of 2,4-disubstituted piperidines without loss of enantiopurity that could be useful building blocks for drug discovery.
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Copyright, Publisher and Additional Information: | © 2022 The Authors. Article available under the CC BY License (https://creativecommons.org/licenses/by/4.0/). | ||||
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Institution: | The University of Sheffield | ||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||
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Depositing User: | Symplectic Sheffield | ||||
Date Deposited: | 08 Sep 2022 10:16 | ||||
Last Modified: | 08 Sep 2022 10:16 | ||||
Status: | Published | ||||
Publisher: | American Chemical Society (ACS) | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1021/acs.joc.2c00862 | ||||
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