Stereochemistry of 1, 3-Eliminative Cyclopropanation
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概要
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The stereochemistry of 1, 3-eliminative cyclopropanation was established in the NaH-catalyzed condensation system involving carbanionic reagents with chlorine and phosphate as the leaving group. It was proved by means of product analysis that the steric course of 1, 3-elimanative cyclopropanation was determined at the 1, 3-eliminative SN2 displacement by the catalyst base, stability of the leaving group and adduct carbanion as well as by solvent polarity, The cis/trans ratios, as well as the optical yeilds of cyclopropane products, agreed closely with the prediction based on the transition state topology at the 1, 3-eliminative cyclization step. It is therefore suggested that the asymmetric Michael type cyclopropanation could be applicable for the absolute assignment of configuration to chiral cyclopropanes.
- 社団法人 日本農芸化学会の論文
著者
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INOUYE Yuzo
Institute for Chemical Research, Kyoto University
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NISHIYAMA Kazuyoshi
Mimasaka Women College
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