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Paper | Regular issue | Vol 41, No. 5, 1995, pp.973-982
Published online, 1st January, 1970
DOI: 10.3987/COM-94-7009
A Convenient Approach to the N-Substituted Amino Dienes, N-Benzyl-5-ethenyl-3,4-dihydropyridin-2-one and N-Cbz-5-Ethenyl-1,2,3,4-tetrahydropyridine

Chiara Bigogno, Bruno Danieli, Giordano Lesma, and Daniele Passarella*

*Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Centro CNR di Studio per le Sostanze Organiche Naturali, Via Venezian 21, 20133 Milano, Italy

Abstract

A synthesis of N-substituted amino dienes (1a) and (1b) is described according to two different approaches. 1a is obtained through condensation of methyl 4-formyl-6-selenophenylhexanoate (4) with benzylamine followed by oxidation and elimination; 1b is formed by a Pd-catalyzed cross-coupling reaction utilizing vinyltributyltin. The preparation of 4 is also described.