Cargando…

Vicinal Diamination of Alkenes under Rh-Catalysis

[Image: see text] The synthesis of 1,2-diamines has been achieved through a single-step, tandem sequence involving Rh-catalyzed aziridination followed by NaI-promoted rearrangement to an isomeric cyclic sulfamide. Facile ring opening of these products in hot water and pyridine affords differentially...

Descripción completa

Detalles Bibliográficos
Autores principales: Olson, David E., Su, Justin Y., Roberts, D. Allen, Du Bois, J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183635/
https://www.ncbi.nlm.nih.gov/pubmed/25233140
http://dx.doi.org/10.1021/ja506532h
_version_ 1782337731080224768
author Olson, David E.
Su, Justin Y.
Roberts, D. Allen
Du Bois, J.
author_facet Olson, David E.
Su, Justin Y.
Roberts, D. Allen
Du Bois, J.
author_sort Olson, David E.
collection PubMed
description [Image: see text] The synthesis of 1,2-diamines has been achieved through a single-step, tandem sequence involving Rh-catalyzed aziridination followed by NaI-promoted rearrangement to an isomeric cyclic sulfamide. Facile ring opening of these products in hot water and pyridine affords differentially protected vicinal diamines. Demonstration of the utility of this method for the syntheses of (±)-enduracididine and (±)-allo-enduracididine is highlighted.
format Online
Article
Text
id pubmed-4183635
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-41836352015-09-18 Vicinal Diamination of Alkenes under Rh-Catalysis Olson, David E. Su, Justin Y. Roberts, D. Allen Du Bois, J. J Am Chem Soc [Image: see text] The synthesis of 1,2-diamines has been achieved through a single-step, tandem sequence involving Rh-catalyzed aziridination followed by NaI-promoted rearrangement to an isomeric cyclic sulfamide. Facile ring opening of these products in hot water and pyridine affords differentially protected vicinal diamines. Demonstration of the utility of this method for the syntheses of (±)-enduracididine and (±)-allo-enduracididine is highlighted. American Chemical Society 2014-09-18 2014-10-01 /pmc/articles/PMC4183635/ /pubmed/25233140 http://dx.doi.org/10.1021/ja506532h Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Olson, David E.
Su, Justin Y.
Roberts, D. Allen
Du Bois, J.
Vicinal Diamination of Alkenes under Rh-Catalysis
title Vicinal Diamination of Alkenes under Rh-Catalysis
title_full Vicinal Diamination of Alkenes under Rh-Catalysis
title_fullStr Vicinal Diamination of Alkenes under Rh-Catalysis
title_full_unstemmed Vicinal Diamination of Alkenes under Rh-Catalysis
title_short Vicinal Diamination of Alkenes under Rh-Catalysis
title_sort vicinal diamination of alkenes under rh-catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183635/
https://www.ncbi.nlm.nih.gov/pubmed/25233140
http://dx.doi.org/10.1021/ja506532h
work_keys_str_mv AT olsondavide vicinaldiaminationofalkenesunderrhcatalysis
AT sujustiny vicinaldiaminationofalkenesunderrhcatalysis
AT robertsdallen vicinaldiaminationofalkenesunderrhcatalysis
AT duboisj vicinaldiaminationofalkenesunderrhcatalysis