- Reactions of Enolates with Vinyl Selenoxides and Vinyl Selenones. One-Step Synthesis of Cyclopropylcarbonyl Compounds
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In the reactions with enolate anions, organoselenium moieties of aryl vinyl selenoxides and selenones have exhibited two important roles, e.g., activation of C=C bonds for conjugate addition reaction and behaviors as excellent leaving groups.Owing to such characteristic fetaures, ketone enolates react with p-chlorophenyl vinyl selenoxide to afford the corresponding cyclopropyl ketones through an initial conjugate addition followed by substitution processes.On the other hand, use of vinyl selenones usually gives much better results with anionic species of active methylene compounds.Vinyl selenones bearing hydroxyl, ketone, and ester groups can also be employed equally well for this type of transformation.
- Ando, Ryoichi,Sugawara, Tomoo,Shimizu, Makoto,Kuwajima, Isao
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p. 2897 - 2904
(2007/10/02)
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- REGIO- AND SITE-SELECTIVE ACTIVATION OF CARBON-CARBON DOUBLE BONDS TO NUCLEOPHILIC REAGENTS. CYCLOPROPANATION OF VINYLSELENONES WITH ACTIVE METHYLENE COMPOUNDS
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Treatment of vinylselenones with active methylene compounds in basic media leads to the formation of cyclopropanes in excellent yields via an addition-substitution reaction.
- Kuwajima, Isao,Ando, Ryoichi,Sugawara, Tomoo
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p. 4429 - 4432
(2007/10/02)
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- Aryl Vinyl Selenoxide as a Versatile Reagent for Transfer of an Ethylene Unit to Enolates. New Synthetic Method of Formation of Cyclopropyl Ketones
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The reaction between an aryl vinyl selenoxide and the lithium enolate of a ketone or an ester gave a cyclopropyl carbonyl compound in good yield.
- Shimizu, Makoto,Kuwajima, Isao
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p. 2921 - 2923
(2007/10/02)
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