The stereoselectivity of the reaction of silyl enol ethers with benzaldehyde is explained by using DFT calculations, considering the relative stability of the possible stereoisomers of the biradical intermediates and the coupling between the single occupied molecular orbitals (SOMOs) of those intermediates. The same approach can be used to justify the observed endo stereoselectivity in the reaction of 2,3-dihydrofuran with 2,4,6-trimethylbenzaldehyde and the exo stereoselectivity in the reaction of the same substrate with 2-naphthaldehyde

A DFT study of 1,4-biradical intermediates involved in stereoselective Paternò-Buechi reactions

D'AURIA, Maurizio;RACIOPPI, Rocco
2010-01-01

Abstract

The stereoselectivity of the reaction of silyl enol ethers with benzaldehyde is explained by using DFT calculations, considering the relative stability of the possible stereoisomers of the biradical intermediates and the coupling between the single occupied molecular orbitals (SOMOs) of those intermediates. The same approach can be used to justify the observed endo stereoselectivity in the reaction of 2,3-dihydrofuran with 2,4,6-trimethylbenzaldehyde and the exo stereoselectivity in the reaction of the same substrate with 2-naphthaldehyde
2010
File in questo prodotto:
File Dimensione Formato  
EJOC 2010, 3831.pdf

non disponibili

Tipologia: Documento in Post-print
Licenza: DRM non definito
Dimensione 506.59 kB
Formato Adobe PDF
506.59 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

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/11563/8696
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 10
social impact