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Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of...

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Autores principales: Ngamnithiporn, Aurapat, Jette, Carina I., Bachman, Shoshana, Virgil, Scott C., Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5912103/
https://www.ncbi.nlm.nih.gov/pubmed/29732133
http://dx.doi.org/10.1039/c7sc05216b
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author Ngamnithiporn, Aurapat
Jette, Carina I.
Bachman, Shoshana
Virgil, Scott C.
Stoltz, Brian M.
author_facet Ngamnithiporn, Aurapat
Jette, Carina I.
Bachman, Shoshana
Virgil, Scott C.
Stoltz, Brian M.
author_sort Ngamnithiporn, Aurapat
collection PubMed
description The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of enantioselectivity (up to 90% ee) on a range of unactivated allylic alcohols for both lactone and lactam nucleophiles. The utility of this method is further highlighted via a number of synthetically useful product transformations.
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spelling pubmed-59121032018-05-04 Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols Ngamnithiporn, Aurapat Jette, Carina I. Bachman, Shoshana Virgil, Scott C. Stoltz, Brian M. Chem Sci Chemistry The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of enantioselectivity (up to 90% ee) on a range of unactivated allylic alcohols for both lactone and lactam nucleophiles. The utility of this method is further highlighted via a number of synthetically useful product transformations. Royal Society of Chemistry 2018-01-24 /pmc/articles/PMC5912103/ /pubmed/29732133 http://dx.doi.org/10.1039/c7sc05216b Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ngamnithiporn, Aurapat
Jette, Carina I.
Bachman, Shoshana
Virgil, Scott C.
Stoltz, Brian M.
Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
title Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
title_full Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
title_fullStr Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
title_full_unstemmed Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
title_short Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
title_sort nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5912103/
https://www.ncbi.nlm.nih.gov/pubmed/29732133
http://dx.doi.org/10.1039/c7sc05216b
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