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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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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. |
format | Online Article Text |
id | pubmed-5912103 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
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title_fullStr | Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
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title_full_unstemmed | Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
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title_short | Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
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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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