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).
2005
61
3429
3436
A. DEAGOSTINO; M. MIGLIARDI; E. OCCHIATO; C. PRANDI; P. ZAVATTARO; P. VENTURELLO
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/19353
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