Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard

[Image: see text] The unexpected domino coupling and rearrangement of the Cinchona alkaloid skeleton has been found to occur in the reaction of 9-chloro-9-deoxy-alkaloids with Grignards from peri-dihalogenonaphthalene. The cyclization and migration of the central quinuclidinylmethyl group (C9) from...

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Autor principal: Boratyński, Przemysław J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9442652/
https://www.ncbi.nlm.nih.gov/pubmed/35998654
http://dx.doi.org/10.1021/acs.joc.2c01249
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author Boratyński, Przemysław J.
author_facet Boratyński, Przemysław J.
author_sort Boratyński, Przemysław J.
collection PubMed
description [Image: see text] The unexpected domino coupling and rearrangement of the Cinchona alkaloid skeleton has been found to occur in the reaction of 9-chloro-9-deoxy-alkaloids with Grignards from peri-dihalogenonaphthalene. The cyclization and migration of the central quinuclidinylmethyl group (C9) from position C-4′ to position C-3′ of quinoline formed a novel chiral ring system of 5-aza-7H-benzo[no]tetraphene, yielding products of unlike configuration. The proposed reaction pathway involves radical intermediates.
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spelling pubmed-94426522022-09-06 Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard Boratyński, Przemysław J. J Org Chem [Image: see text] The unexpected domino coupling and rearrangement of the Cinchona alkaloid skeleton has been found to occur in the reaction of 9-chloro-9-deoxy-alkaloids with Grignards from peri-dihalogenonaphthalene. The cyclization and migration of the central quinuclidinylmethyl group (C9) from position C-4′ to position C-3′ of quinoline formed a novel chiral ring system of 5-aza-7H-benzo[no]tetraphene, yielding products of unlike configuration. The proposed reaction pathway involves radical intermediates. American Chemical Society 2022-08-23 2022-09-02 /pmc/articles/PMC9442652/ /pubmed/35998654 http://dx.doi.org/10.1021/acs.joc.2c01249 Text en © 2022 The Author. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Boratyński, Przemysław J.
Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
title Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
title_full Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
title_fullStr Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
title_full_unstemmed Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
title_short Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
title_sort stereoselective domino rearrangement peri-annulation of cinchona alkaloid derivatives with 8-bromo-1-naphthyl grignard
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9442652/
https://www.ncbi.nlm.nih.gov/pubmed/35998654
http://dx.doi.org/10.1021/acs.joc.2c01249
work_keys_str_mv AT boratynskiprzemysławj stereoselectivedominorearrangementperiannulationofcinchonaalkaloidderivativeswith8bromo1naphthylgrignard

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