Firth, James, Gelardi, Giacomo, Rayner, Peter John orcid.org/0000-0002-6577-4117 et al. (2 more authors) (2018) A synthetic and spectroscopic investigation of the asymmetric α-lithiation-trapping of six-membered N-Boc heterocycles using Alexakis diamines. Heterocycles. pp. 1288-1303. ISSN 0385-5414
Abstract
The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current ‘best-in-class’ sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 12 May 2020 09:40 |
Last Modified: | 26 Nov 2024 00:43 |
Published Version: | https://doi.org/10.3987/COM-18-S(T)87 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.3987/COM-18-S(T)87 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:160630 |