Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions

N-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ Rh(II)-catalyzed reaction. With aliphatic ami...

Descripción completa

Detalles Bibliográficos
Autores principales: Eremeyeva, Maria, Zhukovsky, Daniil, Dar’in, Dmitry, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7136545/
https://www.ncbi.nlm.nih.gov/pubmed/32280388
http://dx.doi.org/10.3762/bjoc.16.55
_version_ 1783518273445298176
author Eremeyeva, Maria
Zhukovsky, Daniil
Dar’in, Dmitry
Krasavin, Mikhail
author_facet Eremeyeva, Maria
Zhukovsky, Daniil
Dar’in, Dmitry
Krasavin, Mikhail
author_sort Eremeyeva, Maria
collection PubMed
description N-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ Rh(II)-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts.
format Online
Article
Text
id pubmed-7136545
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-71365452020-04-10 Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions Eremeyeva, Maria Zhukovsky, Daniil Dar’in, Dmitry Krasavin, Mikhail Beilstein J Org Chem Letter N-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ Rh(II)-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts. Beilstein-Institut 2020-04-02 /pmc/articles/PMC7136545/ /pubmed/32280388 http://dx.doi.org/10.3762/bjoc.16.55 Text en Copyright © 2020, Eremeyeva et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Eremeyeva, Maria
Zhukovsky, Daniil
Dar’in, Dmitry
Krasavin, Mikhail
Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions
title Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions
title_full Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions
title_fullStr Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions
title_full_unstemmed Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions
title_short Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh(II)-catalyzed X–H insertion reactions
title_sort preparation and in situ use of unstable n-alkyl α-diazo-γ-butyrolactams in rh(ii)-catalyzed x–h insertion reactions
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7136545/
https://www.ncbi.nlm.nih.gov/pubmed/32280388
http://dx.doi.org/10.3762/bjoc.16.55
work_keys_str_mv AT eremeyevamaria preparationandinsituuseofunstablenalkyladiazogbutyrolactamsinrhiicatalyzedxhinsertionreactions
AT zhukovskydaniil preparationandinsituuseofunstablenalkyladiazogbutyrolactamsinrhiicatalyzedxhinsertionreactions
AT darindmitry preparationandinsituuseofunstablenalkyladiazogbutyrolactamsinrhiicatalyzedxhinsertionreactions
AT krasavinmikhail preparationandinsituuseofunstablenalkyladiazogbutyrolactamsinrhiicatalyzedxhinsertionreactions

Ejemplares similares