ORGN 501 |
| The ruthenium-catalyzed Alder-ene reaction between alkynyl boronates and terminal alkenes was investigated. The reactions proceed under mild conditions and a strong directing effect of the boron substituent was found to offer complete regioselectivity for the branched isomer, culminating in the formation of 2,2-dialkyl 1-vinylboronates. Complete stereoselectivity was also observed except in cases where an allylic heteroatom was present in the alkene substrate, in which case an E/Z mixture of the vinyl boronate was obtained. The products generated are useful substrates for transition metal-mediated coupling reactions, such as the Suzuki-Miyaura coupling, allowing efficient access to a variety of substructures found in important natural products. |
|
New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster
Division of Organic Chemistry |