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Paper | Special issue | Vol 62, No. 1, 2004, pp.297-311
Published online, 16th September, 2003
DOI: 10.3987/COM-03-S(P)8
Stereoselective Zirconocene-mediated Ring Transformation of 2-Vinylheterocycles to Vinylcarbocycles

Yuji Hanzawa,* Hiromichi Kiyono, and Takeo Taguchi

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Stereoselective ring transformation of 2-vinylheterocycles to vinylcarbocycles was efficiently carried out by the use of a zirconocene equivalent (“Cp2Zr”). The transformation proceeded through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine ring.