Li, X. and Coldham, I. (2014) Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines by Lithiation and Substitution, with in Situ IR Spectroscopy and Configurational Stability Studies. Journal of the American Chemical Society , 136 (15). pp. 5551-5554.
Abstract
Lithiation of N-Boc-1-phenyltetrahydroisoquinolines was optimized by in situ IR spectroscopy. The kinetics for rotation of the carbamate group and for the enantiomerization of the organolithium were determined. The organolithium is configurationally stable at low temperature, and the asymmetric synthesis of 1,1-disubstituted tetrahydroisoquinolines can be achieved with high yields and high enantiomer ratios. The chemistry was applied to the preparation of FR115427 and provides a way to recycle the undesired enantiomer in the synthesis of solifenacin.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Journal of the American Chemical Society, copyright © American Chemical Society after peer review. To access the final edited and published work see http://dx.doi.org/10.1021/ja500485f. |
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: | 25 Apr 2014 09:29 |
Last Modified: | 03 Nov 2016 02:16 |
Published Version: | http://dx.doi.org/10.1021/ja500485f |
Status: | Published |
Publisher: | American Chemical Society |
Refereed: | No |
Identification Number: | 10.1021/ja500485f |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:78500 |