Event Title
Synthesis of Chiral Silanes
Presentation Type
Poster/Portfolio
Presenter Major(s)
Chemistry
Mentor Information
Randy Winchester
Department
Chemistry
Location
Kirkhof Center KC4
Start Date
10-4-2013 9:00 AM
End Date
10-4-2013 10:00 AM
Keywords
Physical Science
Abstract
Compounds with stereogenic silicon that are chiral can be used in organic synthesis as chiral reagents, as resolving agents, and as chiral polymers. We have examined nucleophilic asymmetric substitution by studying the reaction of a dialkoxy prochiral silane with an organolithium compound in hexanes and ether. These reactions have been shown to produce monosubstituted, chiral silanes in good yield. Specifically, selectivity in the synthesis of a silicon stereocenter from a prochiral dimenthoxysilane was investigated. 1-naphtyllithium was prepared by reaction of 1-bromonaphthalene with t-butyllithium and reacted with dimenthoxymethylphenylsilane to be studied for stereoselectivity. Menthoxymethylnaphthylphenylsilane was synthesized in a 45.1 % yield, and diastereomer excess will be determined by relative peak integrations from NMR data, and independently by GC analysis. We will report on this result and others similar to it in our poster.
Synthesis of Chiral Silanes
Kirkhof Center KC4
Compounds with stereogenic silicon that are chiral can be used in organic synthesis as chiral reagents, as resolving agents, and as chiral polymers. We have examined nucleophilic asymmetric substitution by studying the reaction of a dialkoxy prochiral silane with an organolithium compound in hexanes and ether. These reactions have been shown to produce monosubstituted, chiral silanes in good yield. Specifically, selectivity in the synthesis of a silicon stereocenter from a prochiral dimenthoxysilane was investigated. 1-naphtyllithium was prepared by reaction of 1-bromonaphthalene with t-butyllithium and reacted with dimenthoxymethylphenylsilane to be studied for stereoselectivity. Menthoxymethylnaphthylphenylsilane was synthesized in a 45.1 % yield, and diastereomer excess will be determined by relative peak integrations from NMR data, and independently by GC analysis. We will report on this result and others similar to it in our poster.