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.

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Apr 13th, 2:00 PM Apr 13th, 3:00 PM

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.