Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization

[Image: see text] Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereosel...

Descripción completa

Detalles Bibliográficos
Autores principales: Mantelingu, Kempegowda, Lin, Yingfu, Seidel, Daniel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4251528/
https://www.ncbi.nlm.nih.gov/pubmed/25413125
http://dx.doi.org/10.1021/ol502918g
_version_ 1782347065397870592
author Mantelingu, Kempegowda
Lin, Yingfu
Seidel, Daniel
author_facet Mantelingu, Kempegowda
Lin, Yingfu
Seidel, Daniel
author_sort Mantelingu, Kempegowda
collection PubMed
description [Image: see text] Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures.
format Online
Article
Text
id pubmed-4251528
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-42515282015-11-03 Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization Mantelingu, Kempegowda Lin, Yingfu Seidel, Daniel Org Lett [Image: see text] Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures. American Chemical Society 2014-11-03 2014-11-21 /pmc/articles/PMC4251528/ /pubmed/25413125 http://dx.doi.org/10.1021/ol502918g Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Mantelingu, Kempegowda
Lin, Yingfu
Seidel, Daniel
Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
title Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
title_full Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
title_fullStr Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
title_full_unstemmed Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
title_short Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization
title_sort intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral c–h functionalization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4251528/
https://www.ncbi.nlm.nih.gov/pubmed/25413125
http://dx.doi.org/10.1021/ol502918g
work_keys_str_mv AT mantelingukempegowda intramolecular32cycloadditionsofazomethineylidesderivedfromsecondaryaminesviaredoxneutralchfunctionalization
AT linyingfu intramolecular32cycloadditionsofazomethineylidesderivedfromsecondaryaminesviaredoxneutralchfunctionalization
AT seideldaniel intramolecular32cycloadditionsofazomethineylidesderivedfromsecondaryaminesviaredoxneutralchfunctionalization

Ejemplares similares