Synthesis of (−)-cytisine using a 6-endo aza-Michael addition

Synthesis of (−)-cytisine using a 6-endo aza-Michael addition

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 oxazolidin...

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Main Authors: Barát, Viktor, Csókás, Dániel, Bates, Roderick Wayland
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2019
Subjects:
Chemistry
Science::Chemistry::Organic chemistry
Stereochemistry
Online Access:https://hdl.handle.net/10356/83277
http://hdl.handle.net/10220/50076
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-832772023-02-28T19:32:37Z Synthesis of (−)-cytisine using a 6-endo aza-Michael addition Barát, Viktor Csókás, Dániel Bates, Roderick Wayland School of Physical and Mathematical Sciences Chemistry Science::Chemistry::Organic chemistry Stereochemistry 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. MOE (Min. of Education, S’pore) Accepted version 2019-10-03T02:49:29Z 2019-12-06T15:19:01Z 2019-10-03T02:49:29Z 2019-12-06T15:19:01Z 2018 Journal Article 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 0022-3263 https://hdl.handle.net/10356/83277 http://hdl.handle.net/10220/50076 10.1021/acs.joc.8b01156 en The Journal of Organic Chemistry 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 29 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Chemistry
Science::Chemistry::Organic chemistry
Stereochemistry
spellingShingle Chemistry
Science::Chemistry::Organic chemistry
Stereochemistry
Barát, Viktor
Csókás, Dániel
Bates, Roderick Wayland
Synthesis of (−)-cytisine using a 6-endo aza-Michael addition
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Barát, Viktor
Csókás, Dániel
Bates, Roderick Wayland
format Article
author Barát, Viktor
Csókás, Dániel
Bates, Roderick Wayland
author_sort Barát, Viktor
title Synthesis of (−)-cytisine using a 6-endo aza-Michael addition
title_short Synthesis of (−)-cytisine using a 6-endo aza-Michael addition
title_full Synthesis of (−)-cytisine using a 6-endo aza-Michael addition
title_fullStr Synthesis of (−)-cytisine using a 6-endo aza-Michael addition
title_full_unstemmed Synthesis of (−)-cytisine using a 6-endo aza-Michael addition
title_sort synthesis of (−)-cytisine using a 6-endo aza-michael addition
publishDate 2019
url https://hdl.handle.net/10356/83277
http://hdl.handle.net/10220/50076
_version_ 1759854915501424640

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