Nicole Gibbons ACF Abstract FY11

"Chiral silanes by asymmetric substitution at silicon"

Conference Name: 241st National Meeting of the American Chemical Society

We will present progress we have made towards the synthesis of chiral at
silicon asymmetric molecules. Chiral silanes have potential as resolving agents, chiral ligands, chiral auxiliaries and in chiral polymers. We have been investigating nucleophilic asymmetric substitution using prochiral dihydro and dialkoxy silanes. Reaction of these with organolithium compounds in the presence of chiral diamines, leads to monosubstitution and chiral silanes in good yields and modest enantiomeric excess. Recently Tomooka, et. al. (1) have reported good enantioselectivity with 2,2-Bis((4-s)-(-)-4-isopropyloxazoline)propane, (BIP) catalyst on cyclic dialkoxy silanes. We will be presenting a comparison of our previous results with sparteine as a catalyst to new results studying BIP as a catalyst. (1) Kazunobu Igawa, Junko Takada, Tomohiro Shimono, and Katsuhiko Tomooka; J. Am. Chem. Soc. 2008, 130, 1613216133, -- Nicole Gibbons