ORGN 528 |
| Oxasilacyclopentenes, which serve as useful intermediates in organic synthesis, were efficiently produced in a one-step reaction from carbonyls and alkynylsilanes in the presence of a catalytic amount of metal alkoxide. The reaction proceeds readily at room temperature and is tolerant of a wide variety of carbonyl substrates; however, only small variations in the steric and stereoelectronic environment on the alkynylsilane are permitted. Mechanistic aspects and parameters that influence the efficiency of the reaction, such as the substituents on the silyl and alkynyl groups as well as the metal alkoxide, will be discussed. Overall, the transformation represents a one-pot synthesis of cyclic vinylsilane-containing silyl ethers via a novel tandem alkynylation-hydrosilylation. |
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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 |