2-Chloro-2-cyclopropylideneacetates (1-Me and 1-Et) and their spiropentane analogues 2 cycloadd enantiopure five-membered cyclic nitrones to give the corresponding adducts (quantitatively, four examples), which undergo cascade ring enlargements to yield indolizinone derivatives (53-70%, four examples). The ring enlargement process is triggered by the abstraction of a bridgehead proton induced by a base and can be suppressed by the presence of a bulky substituent nearby, such as a (triisopropylsilyl)- oxy group.

Synthesis of Enantiopure Indolizinones by Cascade Ring Enlargements of 4'-Chlorospiro[cyclopropane-1,5'-isoxazolidines] / J. Revuelta; S. Cicchi; C. Faggi; S. I. Kozhushkov; A. de Meijere; A. Brandi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 71:(2006), pp. 2417-2423. [10.1021/jo052564x]

Synthesis of Enantiopure Indolizinones by Cascade Ring Enlargements of 4'-Chlorospiro[cyclopropane-1,5'-isoxazolidines]

REVUELTA CRESPO, JULIA MARIA;CICCHI, STEFANO;FAGGI, CRISTINA;BRANDI, ALBERTO
2006

Abstract

2-Chloro-2-cyclopropylideneacetates (1-Me and 1-Et) and their spiropentane analogues 2 cycloadd enantiopure five-membered cyclic nitrones to give the corresponding adducts (quantitatively, four examples), which undergo cascade ring enlargements to yield indolizinone derivatives (53-70%, four examples). The ring enlargement process is triggered by the abstraction of a bridgehead proton induced by a base and can be suppressed by the presence of a bulky substituent nearby, such as a (triisopropylsilyl)- oxy group.
2006
71
2417
2423
J. Revuelta; S. Cicchi; C. Faggi; S. I. Kozhushkov; A. de Meijere; A. Brandi
File in questo prodotto:
File Dimensione Formato  
JOC052564_Ciclopropilideneacetato.pdf

Accesso chiuso

Tipologia: Versione finale referata (Postprint, Accepted manuscript)
Licenza: Tutti i diritti riservati
Dimensione 140.46 kB
Formato Adobe PDF
140.46 kB Adobe PDF   Richiedi una copia

I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/312301
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 16
  • ???jsp.display-item.citation.isi??? 15
social impact