ORGN 142 |
| Stephen A. Westcott1, Christopher M. Vogels1, and R. Tom Baker2. (1) Department of Chemistry, Mount Allison University, 63C York Street, Sackville, NB E4L 1G8, Canada, (2) Chemistry Division, Los Alamos National Laboratory, MS J514, Los Alamos, NM 87545 |
| The hydroboration of alkenes and alkynes, which constitutes the addition of a B-H bond across a carbon-carbon multiple bond, is an extremely important reaction in organic synthesis. Although simple boron hydride reagents such as borane and 9-borabicyclo[3.3.1]nonane react readily with alkenes at room temperature, hydroborations with catecholborane (HBcat) generally require elevated temperatures. The discovery that transition metals can be used to catalyze the addition of HBcat to organic substrates has become an important and well-established technique. These reactions can have regio-, chemo-, or stereoselectivities, complementary, or more remarkably, opposite to those from products obtained via the uncatalyzed variant. We report herein that rhodium catalyzed hydroborations of sulfur-containing substrates can be used to give the corresponding thioboronate ester derivatives. |
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |