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Paper | Special issue | Vol 76, No. 2, 2008, pp.1141-1154
Published online, 29th May, 2008
DOI: 10.3987/COM-08-S(N)73
Regioselective Synthesis of Either 1H- or 2H-1,2,3-Triazoles via Michael Addition to α,β-Unsaturated Ketones

Sen Wai Kwok, Jason E. Hein, Valery V. Fokin, and K. Barry Sharpless*

*Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, BCC 315, La Jolla, CA 92037, USA


The Michael reaction of NH-1,2,3-triazole (1) with α,β-unsaturated ketones was studied. 1H-1,2,3-triazolyl-ketones were selectively generated when 1 was combined neat with a variety of enones. The use of aprotic solvents with catalytic base gave the corresponding 2H-regioisomers. Together, these two protocols provide direct access to either the N1- or N2-substituted 1,3-triazolyl ketone regioisomers.