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Paper | Special issue | Vol 52, No. 2, 2000, pp.633-642
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S59
Synthesis of 3-Allyl- and 3-Benzyl-Δ3-cephems through Sequential Reductive 1,2-Elimination/Addition/Cyclization of 3,4-Disubstituted 2-Butenoates in Allyl and Benzyl Halides/Mn/NiCl2/AlCl3/NMP Systems

Hideo Tanaka,* Yoshihisa Tokumaru, and Sigeru Torii

*Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan

Abstract

One-pot synthesis of 3-allyl- and 3-benzyl-Δ3-cephems through a sequential reductive 1,2-elimination/addition/cyclization of 3,4-disubstituted 2-[2-oxo-3-phenylacetamido-4-(phenylsulfonylthio)azetidin-1-yl]-2-butenoates was successfully performed by treatment with allyl and benzyl halides in an Mn/NiCl2(bpy)/AlCl3/N-methyl-2-pyrroridinone (NMP) system.