A novel approach to useful aminols for the synthesis of carbocyclic nucleosides is reported starting from a convenient source, the 2-azanorborn-5-enes. These are readily available through the Grieco cycloaddition of cyclopentadiene with iminium salts and are reactive dipolarophiles toward nitrile oxides. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target aminols through the unmasking of the hydroxymethylene group at the C3 level of the azanorbornene structure.

Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels–Alder reactions

QUADRELLI, PAOLO;PICCANELLO, ANDREA;BOVIO, BRUNA;MELLA, MARIELLA;CARAMELLA, PIERLUIGI
2006

Abstract

A novel approach to useful aminols for the synthesis of carbocyclic nucleosides is reported starting from a convenient source, the 2-azanorborn-5-enes. These are readily available through the Grieco cycloaddition of cyclopentadiene with iminium salts and are reactive dipolarophiles toward nitrile oxides. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target aminols through the unmasking of the hydroxymethylene group at the C3 level of the azanorbornene structure.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/137855
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 22
  • ???jsp.display-item.citation.isi??? 22
social impact