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; Sigeru Torii

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, Sigeru Torii

Faculty of Engineering

Research output: Contribution to journal › Article

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	633-642
Number of pages	10
Journal	Heterocycles
Volume	52
Issue number	2
DOIs	https://doi.org/10.3987/COM-99-S59
Publication status	Published - Feb 1 2000

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ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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Tanaka, H., Tokumaru, Y., & Torii, S. (2000). 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. Heterocycles, 52(2), 633-642. https://doi.org/10.3987/COM-99-S59

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10.3987/COM-99-S59