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.

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Apr 10th, 9:00 AM Apr 10th, 10:00 AM

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.