Searching for Cyclin-Dependent Kinase Inhibitors Using a New Variant of the Cope Elimination
Roger J. Griffin,* Andrew Henderson, Nicola J. Curtin, Aude Echalier, Jane A. Endicott, Ian R. Hardcastle, David R. Newell, Martin E. M. Noble, Lan-Zhen Wang and Bernard T. Golding*
*Northern Institute for Cancer Research, School of Natural Sciences - Chemistry, Bedson Building, University of Newcastle, Newcastle upon Tyne, NE1 7RU, U.K. , Email: b.t.goldingncl.ac.uk
R. J. Gruffin, A. Henderson, N. J. Curtin, A. Echalier, J. A. Endicott, I. R. Hardcastle, D. R. Newell, M. E. M. Noble, L.-Z. Wang, B. T. Golding, J. Am. Chem. Soc., 2006, 128, 6012-6013.
DOI: 10.1021/ja060595j (free Supporting Information)
β-Piperidinoethylsulfides can be oxidized by m-chloroperbenzoic acid to intermediates containing both N-oxide and sulfone functions. These undergo a Cope-type elimination to a vinylsulfone that can be captured by amines to afford β-aminoethylsulfones. The synthetic methodology developed can be utilized in multiple-parallel format and has numerous potential applications in medicinal chemistry.
see article for more examples
proposed reaction pathway