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Abstract

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Note | Special issue | Vol 64, No. 1, 2004, pp. 467 - 474
Published online: 30th July, 2004
DOI: 10.3987/COM-04-S(P)10
Organolanthanide Catalyzed Intramolecular 5-endo-dig Hydroamination: An Unusual Anti-Markovnikov Cyclization

Gary A. Molander* and Hikaru Hasegawa

*Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, U.S.A.

Abstract

Intramolecular 5-endo-dig hydroaminations of homopropargylamine derivatives were efficiently catalyzed by the organolanthanide precatalyst, Cp*2YbCH(TMS)2 (Cp* = C5Me5), to give the endocyclic enamine products. The 5-endo-dig hydroamination was also preferred in the presence of another olefin that would afford a 6-exo cyclization.

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