Synthesis, stereochemistry, and reactions of 2,5-diphenylsilacyclopentenes |
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Authors: | Yukinori Nagao Chikashi Kimura Kozo Kozawa Michael E Jung |
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Institution: | 1. Department of Industrial Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan 2. Department of Chemistry and Biochemistry, University of California at Los Angeles, 405 Hilgard Avenue, Los Angeles, CA, 90095, USA
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Abstract: | 1,1-Disubstituted derivatives of 2,5-diphenylsilacyclopent-3-enes, namely those having the 1,1-diphenyl, 1,1-dimethyl, 1-alkoxy-1-methyl and 1,1-dialkoxy, were prepared by a one-pot reaction of (1E, 3E)-1,4-diphenyl-1,3-butadiene and dichlorosilanes in the presence of magnesium. Each silacyclopentene was formed as a mixture of one trans and two cis isomers. 1-Ethoxy-1-methyl-2,5-diphenylsilacyclopent-3-ene and 1,1-diethoxy-2,5-diphenylsilacyclopent-3-ene were reacted with optically active alcohols to furnish the corresponding diastereomers. The absolute configuration of one of these diastereomers was determined by X-ray structure analysis. The mixture of cis and trans diastereomers was lithiated by lithium diisopropylamide (LDA) to obtain the trans forms selectively, with the stereoselectivity being determined by NOE experiments. |
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