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Paper | Special issue | Vol 77, No. 1, 2009, pp.311-321
Published online, 10th July, 2008
DOI: 10.3987/COM-08-S(F)18
Ring Contraction of α,β-Unsaturated Cyclic Amines with cis-Dihydroxylation at the α,β-Position

Samuel S. Libendi, Yosuke Demizu, Yoshihiro Matsumura, and Osamu Onomura*

*Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

α,β-Unsaturated cyclic amines are oxidized by OsO4 to afford α,β-cis-dihydroxylated compounds which are thermodynamically transformed into ring-opened keto-alcohols. The keto-alcohols are then cyclized to form synthetically useful ring-contracted cyclic amines.