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https://hdl.handle.net/10356/83277| Title: | Synthesis of (−)-cytisine using a 6-endo aza-Michael addition | Authors: | Barát, Viktor Csókás, Dániel Bates, Roderick Wayland |
Keywords: | Chemistry Science::Chemistry::Organic chemistry Stereochemistry |
Issue Date: | 2018 | Source: | Barát, V., Csókás, D., & Bates, R. W. (2018). Synthesis of (−)-cytisine Using a 6- endo aza-Michael addition. The Journal of Organic Chemistry, 83(16), 9088-9095. doi:10.1021/acs.joc.8b01156 | Series/Report no.: | The Journal of Organic Chemistry | Abstract: | An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair. | URI: | https://hdl.handle.net/10356/83277 http://hdl.handle.net/10220/50076 |
ISSN: | 0022-3263 | DOI: | 10.1021/acs.joc.8b01156 | Schools: | School of Physical and Mathematical Sciences | Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.8b01156 | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
| Appears in Collections: | SPMS Journal Articles |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| Cytisine JOC revised.pdf | accepted manuscript | 6.37 MB | Adobe PDF |  View/Open |
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