Talk, R.A., Duperray, A., Li, X. et al. (1 more author) (2016) Synthesis of substituted tetrahydroisoquinolines by lithiation then electrophilic quench. Organic and Biomolecular Chemistry, 14 (21). pp. 4908-4917. ISSN 1477-0520
Abstract
Substituted N-tert-butoxycarbonyl (Boc)-1,2,3,4-tetrahydroisoquinolines were prepared and treated with n-butyllithium in THF at −50 °C to test the scope of the metallation and electrophilic quench. The lithiation was optimised by using in situ ReactIR spectroscopy and the rate of rotation of the carbamate was determined. The 1-lithiated intermediates could be trapped with a variety of electrophiles to give good yields of 1-substituted tetrahydroisoquinoline products. Treatment with acid or reduction with LiAlH4 allows conversion to the N–H or N–Me compound. The chemistry was applied to the efficient total syntheses of the alkaloids (±)-crispine A and (±)-dysoxyline.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Royal Society of Chemistry 2016. This is an author produced version of a paper subsequently published in Organic and Biomolecular Chemistry. Uploaded in accordance with the publisher's self-archiving policy. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 02 Aug 2016 11:30 |
Last Modified: | 03 Nov 2017 05:38 |
Published Version: | http://dx.doi.org/10.1039/C6OB00577B |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Refereed: | Yes |
Identification Number: | 10.1039/C6OB00577B |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:103199 |