ORGN 575 |
| Grubbs' 2nd generation catalyst was found to dimerize diazoacetates highly stereoselectivity (to cis-olefins). Interestingly, diazo coupling in the presence of an olefin resulted in dimerization of both the diazoacetate and the olefin, without any accompanying cross-metathesis or cyclopropanation. These results, illustrating the ability of Grubbs' catalyst to catalyze both diazoacetate dimerization and alkene metathesis have been applied to the synthesis of macrocyclic dienyl dilactones. Dilactones of varying ring sizes (12-26) have been synthesized via head-to-head dimerization of unsaturated diazoacetates (readily available from the corresponding unsaturated alcohols and glyoxylic acid chloride tosyl hydrazone) followed by RCM.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
