Preparation and cycloaddition reactions of enantiopure 2-(N-acylamino)-1, 3-dienes for the synthesis of octahydroquinoline derivatives

FL Galbo, EG Occhiato, A Guarna…

Index: Galbo, Fabrizio Lo; Occhiato, Ernesto G.; Guarna, Antonio; Faggi, Cristina Journal of Organic Chemistry, 2003 , vol. 68, # 16 p. 6360 - 6368

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Citation Number: 58

Abstract

Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions were carried out with a glutarimide-derived vinyl phosphate, bearing a chiral auxiliary on the N atom, to prepare enantiopure 2-(N-acylamino)-1, 3-dienes as partners in Diels-Alder reactions. The cycloadditions were performed with various dienophiles under thermal conditions, with or without Lewis acids. With maleimides, the preferential formation of endo cycloadducts was ...