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Paper | Regular issue | Vol 78, No. 2, 2009, pp.369-387
Published online, 25th September, 2008
DOI: 10.3987/COM-08-11508
■ Studies on the Amino-Heck Reactions of Unsaturated Ketones O-Phosphinyloximes for the Preparation of Substituted Pyridines

Jia-Liang Zhu,* Yi-Lin Su, Yu-Hui Chan, I-Chia Chen, and Chuan-Chen Liao

*Department of Chemistry, National Dong-Hwa University, Hualien 974, Taiwan, R.O.C.

Abstract

The amino-Heck cyclization process has been applied into a range of γ,δ-unsaturated ketone O-diethylphosphinyloximes 1 and δ,ε-unsaturated ketone O-diethylphosphinyloximes 7. Under the specific catalytic conditions developed by us, these substrates were found to preferentially undergo the 6-endo cyclization to give the formation of 2-substituted pyridines 3 and substituted methylpyridines 8, respectively, in moderate to good yields. Besides, several interesting aspects on the effects of phosphinyl groups, solvents, bases and molecular sieves on the regioselectivity of the cyclization of 1 have also been realized.