- Carbon-Carbon Bond-Forming Reactions of Zinc Homoenolate of Esters. A Novel Three-Carbon Nucleophile with General Synthetic Utility
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In the presence of suitable catalysts and additives, the zinc homoenolate of alkyl propionate and its congeners undergo a variety of carbon-carbon bond-forming reactions, e.g., addition onto carbonyl compounds, allylation, arylation, vinylation, and acylation, to produce diverse kinds of alkanoates and cyclopropane derivatives.The moderately reactive zinc homoenolate exhibited a very high degree of chemoselectivity in these reactions.Me3SiCl has been found to greatly accelerate 1,2- or 1,4-addition and the allylation reaction of the zinc reagent.
- Nakamura, Eiichi,Aoki, Satoshi,Sekiya, Kouichi,Oshino, Hiroji,Kuwajima, Isao
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p. 8056 - 8066
(2007/10/02)
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- Catalytic "Homo-Reformatsky" Reaction. Ambident Chemical Reactivities of the Zinc Homoenolate of Propionate
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Zinc halide catalyzed reaction of 1-alkoxy-1-siloxycyclopropane with carbonyl compounds gives 4-siloxy esters, while a related reaction with acid chlorides produces either 4-keto esters or (acyloxy)cyclopropanes.
- Oshino, Hiroji,Nakamura, Eiichi,Kuwajima, Isao
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p. 2802 - 2804
(2007/10/02)
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