Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

The Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,...

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Detalles Bibliográficos
Autores principales: Banfi, Luca, Basso, Andrea, Cerulli, Valentina, Rocca, Valeria, Riva, Renata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170203/
https://www.ncbi.nlm.nih.gov/pubmed/21915196
http://dx.doi.org/10.3762/bjoc.7.109
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author Banfi, Luca
Basso, Andrea
Cerulli, Valentina
Rocca, Valeria
Riva, Renata
author_facet Banfi, Luca
Basso, Andrea
Cerulli, Valentina
Rocca, Valeria
Riva, Renata
author_sort Banfi, Luca
collection PubMed
description The Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,4 asymmetric induction in an Ugi reaction as well as the first example of diastereoselective Ugi reaction of seven membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines.
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spelling pubmed-31702032011-09-13 Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines Banfi, Luca Basso, Andrea Cerulli, Valentina Rocca, Valeria Riva, Renata Beilstein J Org Chem Letter The Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,4 asymmetric induction in an Ugi reaction as well as the first example of diastereoselective Ugi reaction of seven membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines. Beilstein-Institut 2011-07-13 /pmc/articles/PMC3170203/ /pubmed/21915196 http://dx.doi.org/10.3762/bjoc.7.109 Text en Copyright © 2011, Banfi et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Banfi, Luca
Basso, Andrea
Cerulli, Valentina
Rocca, Valeria
Riva, Renata
Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines
title Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines
title_full Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines
title_fullStr Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines
title_full_unstemmed Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines
title_short Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines
title_sort long-range diastereoselectivity in ugi reactions of 2-substituted dihydrobenzoxazepines
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170203/
https://www.ncbi.nlm.nih.gov/pubmed/21915196
http://dx.doi.org/10.3762/bjoc.7.109
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