Event Title
Chiral Silanes by Asymmetric Substitution at Silicon
Presentation Type
Poster/Portfolio
Presenter Major(s)
Chemistry
Mentor Information
Randy Winchester, winchesr@gvsu.edu
Department
Chemistry
Location
Henry Hall Atrium 77
Start Date
13-4-2011 2:00 PM
End Date
13-4-2011 3:00 PM
Keywords
Physical Science
Abstract
We will present progress we have made towards the synthesis of chiral at silicon asymetric 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((4S)-(-)-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 2,2-Bis((4S)-(-)-4-isopropyloxazoline)propane (BIP) as a catalyst. (1) Kazunobu Igawa, Junko Takada, Tomohiro Shimono, and Katsuhiko Tomooka; J. Am. Chem. Soc. 2008, 130, 16132, 16133.
Chiral Silanes by Asymmetric Substitution at Silicon
Henry Hall Atrium 77
We will present progress we have made towards the synthesis of chiral at silicon asymetric 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((4S)-(-)-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 2,2-Bis((4S)-(-)-4-isopropyloxazoline)propane (BIP) as a catalyst. (1) Kazunobu Igawa, Junko Takada, Tomohiro Shimono, and Katsuhiko Tomooka; J. Am. Chem. Soc. 2008, 130, 16132, 16133.