Studies on the development of catalytic protocols for asymmetric allylboration of carbonyl compounds using pinene based boron reagents

ORGN 160

Kanth V. B. Josyula, kjosyula@sial.com1, Subash C. Jonnalagadda, sjonnala@d.umn.edu2, and Venkatram R. Mereddy, vmereddy@d.umn.edu2. (1) New Product Research & Development, Aldrich Chemical Company, 6000 N. Teutonia Ave, Milwaukee, WI 53209, (2) Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812
Asymmetric allylboration is an important stereoselective C-C bond-forming reaction in organic synthesis. The (+) and (-) B-Allyldiisopinocampheylboranes [Ipc2B(allyl)] are reagents of choice for asymmetric allylboration of aldehydes. Typically these allylboranes are freshly prepared or generated in situ and used immediately at –78 to –100 °C, since they are unstable for extended periods at ambient temperature. We recently developed new, salt-free, Ipc2B(allyl) reagents as stable solutions in pentane and in dioxane. Under refrigerator storage conditions, no appreciable decomposition is observed even after several months. The reagents exhibit superb reactivity and reactions can be conveniently performed at 5 °C, even in water. Results of studies aimed at developing a catalytic version of this transformation will be presented.

 

Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Sci-Mix

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007