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Paper | Regular issue | Vol 85, No. 2, 2012, pp.383-401
Published online, 29th December, 2011
DOI: 10.3987/COM-11-12396
■ Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes

Sheng-Wei Tsao and Jia-Liang Zhu*

*Department of Chemistry, National Dong Hwa University, 1, Sec. 2, Hsueh Rd., Shou-Feng, Hualien 974, Taiwan, R.O.C.

Abstract

Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 °C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a β-aryl moiety possibly due to the stabilizing π-π stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.