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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
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.
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
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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