Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions of alkynyl phosphonates with bicyclo[2.2.1]hepta-2,5-diene.

Tanner J Kettles, Neil Cockburn, William Tam

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.

The Journal of organic chemistry 2011 Aug 19

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Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions between alkynyl phosphonates and bicyclo[2.2.1]hepta-2,5-diene were studied. The observed reactivity was found to be dependent on the presence of the phosphonate moiety. The Ru-catalyzed cycloaddition was compatible with a variety of aromatic and aliphatic substituted alkynyl phosphonates, providing the corresponding phosphonate substituted deltacyclenes in low to good yields (up to 88%).

Citation

Tanner J Kettles, Neil Cockburn, William Tam. Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions of alkynyl phosphonates with bicyclo[2.2.1]hepta-2,5-diene. The Journal of organic chemistry. 2011 Aug 19;76(16):6951-7