Nucleophilic cyclopropanation reaction with bis(iodozincio)methane by 1,4-addition to alpha,beta-unsaturated carbonyl compounds.
Nucleophilic cyclopropanation reaction with bis(iodozincio)methane by 1,4-addition to alpha,beta-unsaturated carbonyl compounds.
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通过 1,4-加成至 α,β-不饱和羰基化合物与双（碘锌）甲烷发生亲核环丙烷化反应。
DOI：
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
S. Matsubara
中科院分区：
文献类型：
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作者：
K. Nomura;T. Hirayama;S. Matsubara
在三甲基甲硅烷基氰化物存在下，用双(碘锌)甲烷处理在γ位具有亲电子位点的α，β-不饱和酮，以良好的产率提供β-环丙基取代的酮的(Z)-甲硅烷基烯醇醚。该反应通过 1,4-加成形成烯醇化物，并对相邻的亲电位点进行连续的分子内亲核攻击。 γ-乙氧基羰基-α,β-不饱和酮与双(碘锌)甲烷在三甲基甲硅烷基氰存在下反应得到1-乙氧基-1-三甲基甲硅烷氧基环丙烷衍生物，该衍生物可视为高烯醇化物等价物。另外，获得的高烯醇化物等价物与亚胺的反应非对映选择性地得到1-(E)-烯基-2-(1-氨基烷基)链烷醇。
Treatment of alpha,beta-unsaturated ketones with an electrophilic site at the gamma-position in the presence of trimethylsilyl cyanide with bis(iodozincio)methane afforded the (Z)-silyl enol ether of the beta-cyclopropyl substituted ketone in good yields. The reaction proceeds by 1,4-addition to form an enolate, and its sequential intramolecular nucleophilic attack to an adjacent electrophilic site. The reaction of gamma-ethoxycarbonyl-alpha,beta-unsaturated ketone and bis(iodozincio)methane in the presence of trimethylsilyl cyanide afforded 1-ethoxy-1-trimethylsiloxycyclopropane derivatives, which can be regarded as the homoenolate equivalent. Additionally, reaction of the obtained homoenolate equivalents with imines give 1-(E)-alkenyl-2-(1-aminoalkyl)alkanols diastereoselectively.
影响因子：
16.6
作者：
Brown, M. Kevin;May, Tricia L.;Hoveyda, Amir H.
通讯作者：
Hoveyda, Amir H.
DOI：
10.1021/jo016413f
发表时间：
2002-05
期刊：
The Journal of organic chemistry
影响因子：
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作者：
W. Roush;T. Bannister;M. Wendt;J. A. Jablonowski;K. Scheidt
通讯作者：
W. Roush;T. Bannister;M. Wendt;J. A. Jablonowski;K. Scheidt