Logo del repository
  1. Home
 
Opzioni

Arylsulfonyl Groups: The Best Cyclization Auxiliaries for the Preparation of ATRC γ-Lactams can be Acidolytically Removed

A. J. Clark
•
A. Cornia
•
FELLUGA, FULVIA
altro
D. Spinelli
2014
  • journal article

Periodico
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Abstract
The N-arylsulfonyl group, which is the best and most useful cyclization auxiliary for the transition-metal-catalyzed atom transfer radical cyclization (ATRC) of N-allyl-α-polychloroamides, can be effectively removed from the target γ-lactams by using H2SO4–HOAc, without impairing the halogen functions. The reaction involves H+ attack on the aromatic moiety, and is strongly responsive to the electronic properties of the substituent bound to the aromatic ring: electron-donating groups, such as methyl or methoxy are, in fact, required for efficient “deprotection”. The N-p-nitrophenylsulfonyl cyclization auxiliary, in contrast to all the other sulfonyl groups tested, proved to be unsuitable for the ATRC, owing to a side reductive transposition that halts the redox cycle
DOI
10.1002/ejoc.201402769
WOS
WOS:000343872900019
Archivio
http://hdl.handle.net/11368/2809534
info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-84908042155
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201402769/abstract;jsessionid=3B58123F74D61C83C76EC79CD1DE3026.f03t03?systemMessage=Wiley+Online+Library+will+be+disrupted+on+the+18th+October+from+10%3A00+BST+%2805%3A00+EDT%29+for+essential+maintenance+for+approximately+two+hours+as+we+make+upgrades+to+improve+our+services+to+you
Diritti
metadata only access
Soggetti
  • Protecting group

  • Deprotection

  • Lactam

  • Radical

  • Cyclization

  • Amides

Web of Science© citazioni
17
Data di acquisizione
Mar 2, 2024
google-scholar
Get Involved!
  • Source Code
  • Documentation
  • Slack Channel
Make it your own

DSpace-CRIS can be extensively configured to meet your needs. Decide which information need to be collected and available with fine-grained security. Start updating the theme to match your nstitution's web identity.

Need professional help?

The original creators of DSpace-CRIS at 4Science can take your project to the next level, get in touch!

Realizzato con Software DSpace-CRIS - Estensione mantenuta e ottimizzata da 4Science

  • Impostazioni dei cookie
  • Informativa sulla privacy
  • Accordo con l'utente finale
  • Invia il tuo Feedback