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Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates
[Image: see text] A highly efficient method for the enantioselective one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes has been reported. The reaction proceeds via the formation of hemiaminal intermediates obtained by the enantioselective addition of respective alcohols to imines catalyzed by...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4136672/ https://www.ncbi.nlm.nih.gov/pubmed/25075467 http://dx.doi.org/10.1021/ol501789c |
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author | Nimmagadda, Sri Krishna Zhang, Zuhui Antilla, Jon C. |
author_facet | Nimmagadda, Sri Krishna Zhang, Zuhui Antilla, Jon C. |
author_sort | Nimmagadda, Sri Krishna |
collection | PubMed |
description | [Image: see text] A highly efficient method for the enantioselective one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes has been reported. The reaction proceeds via the formation of hemiaminal intermediates obtained by the enantioselective addition of respective alcohols to imines catalyzed by a chiral magnesium phosphate catalyst, followed by intramolecular cyclization under mildly basic conditions. A wide range of substrates have been converted to the respective chiral heterocyclic products in high yields and with excellent enantioselectivities using this one-pot procedure. |
format | Online Article Text |
id | pubmed-4136672 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41366722015-07-30 Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates Nimmagadda, Sri Krishna Zhang, Zuhui Antilla, Jon C. Org Lett [Image: see text] A highly efficient method for the enantioselective one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes has been reported. The reaction proceeds via the formation of hemiaminal intermediates obtained by the enantioselective addition of respective alcohols to imines catalyzed by a chiral magnesium phosphate catalyst, followed by intramolecular cyclization under mildly basic conditions. A wide range of substrates have been converted to the respective chiral heterocyclic products in high yields and with excellent enantioselectivities using this one-pot procedure. American Chemical Society 2014-07-30 2014-08-15 /pmc/articles/PMC4136672/ /pubmed/25075467 http://dx.doi.org/10.1021/ol501789c Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Nimmagadda, Sri Krishna Zhang, Zuhui Antilla, Jon C. Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates |
title | Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and
1,3-Oxazinanes via Hemiaminal Intermediates |
title_full | Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and
1,3-Oxazinanes via Hemiaminal Intermediates |
title_fullStr | Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and
1,3-Oxazinanes via Hemiaminal Intermediates |
title_full_unstemmed | Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and
1,3-Oxazinanes via Hemiaminal Intermediates |
title_short | Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and
1,3-Oxazinanes via Hemiaminal Intermediates |
title_sort | asymmetric one-pot synthesis of 1,3-oxazolidines and
1,3-oxazinanes via hemiaminal intermediates |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4136672/ https://www.ncbi.nlm.nih.gov/pubmed/25075467 http://dx.doi.org/10.1021/ol501789c |
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