It is demonstrated that alpha,beta-unsaturated acetals can be considered a synthetic tool for transforming carbonyl derivatives into cheap and easily accessible starting materials for the construction of various and more complex structures. The lithium-potassium mixed superbase LIC-KOR induces a conjugate elimination reaction that converts alpha,beta-unsaturated acetals into IE-1-alkoxybuta-1,3-dienes. These derivatives can be readily metalated in situ and functionalized by reaction with electrophiles. The results can be grouped in two sections: (1) the palladium-catalyzed cross-coupling reaction between alkoxydienylboronates and tetralone- or isochromanone-derived vinyl triflates; (2) the regio- and stereoselective cross coupling reaction with aryl derivatives in the presence of a palladium catalyst (Heck conditions).

LIC-KOR PROMOTED FORMATION OF CONJUGATE DIENES AS USEFUL BUILDING BLOCKS IN PALLADIUM-CATALYZED SYNTHESES / A. DEAGOSTINO; M. MIGLIARDI; E. OCCHIATO; C. PRANDI; P. ZAVATTARO; P. VENTURELLO. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 61:(2005), pp. 3429-3436. [10.1016/j.tet.2005.01.044]

LIC-KOR PROMOTED FORMATION OF CONJUGATE DIENES AS USEFUL BUILDING BLOCKS IN PALLADIUM-CATALYZED SYNTHESES

OCCHIATO, ERNESTO GIOVANNI;
2005

Abstract

It is demonstrated that alpha,beta-unsaturated acetals can be considered a synthetic tool for transforming carbonyl derivatives into cheap and easily accessible starting materials for the construction of various and more complex structures. The lithium-potassium mixed superbase LIC-KOR induces a conjugate elimination reaction that converts alpha,beta-unsaturated acetals into IE-1-alkoxybuta-1,3-dienes. These derivatives can be readily metalated in situ and functionalized by reaction with electrophiles. The results can be grouped in two sections: (1) the palladium-catalyzed cross-coupling reaction between alkoxydienylboronates and tetralone- or isochromanone-derived vinyl triflates; (2) the regio- and stereoselective cross coupling reaction with aryl derivatives in the presence of a palladium catalyst (Heck conditions).
61
3429
3436
A. DEAGOSTINO; M. MIGLIARDI; E. OCCHIATO; C. PRANDI; P. ZAVATTARO; P. VENTURELLO
File in questo prodotto:
File Dimensione Formato  
TETR_2005.pdf

Accesso chiuso

Descrizione: articolo
Tipologia: Pdf editoriale (Version of record)
Licenza: DRM non definito
Dimensione 378.82 kB
Formato Adobe PDF
378.82 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in FLORE 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: http://hdl.handle.net/2158/19353
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 21
  • ???jsp.display-item.citation.isi??? 20
social impact