首页> 外文期刊>The Journal of Organic Chemistry >An efficient stereocontrolled strategy in the cyclopropanation reactions of α,β-unsaturated ketones with semistabilized ylides: highly selective synthesis of two geometrical isomers of vinyl-substituted cyclopropane derivatives
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An efficient stereocontrolled strategy in the cyclopropanation reactions of α,β-unsaturated ketones with semistabilized ylides: highly selective synthesis of two geometrical isomers of vinyl-substituted cyclopropane derivatives

机译:α,β-不饱和酮与半稳定化化合物的环丙烷化反应中的有效立体控制策略:乙烯基取代的环丙烷衍生物的两种几何异构体的高选择性合成

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摘要

The semistabilized telluronium ylides 2a-e, generated in situ from the corresponding telluronium salts 1a-e, reacted with α,β-unsaturated ketones 6a-d to afford cis-2-vinyl-trans-3-substituted cyclopropyl ketones with high stereoselectivity and in high to excellent yields. Conversely, these enones gave trans-2-vinyl-trans-3-substituted cyclopropyl ketones, when the corresponding arsonium ylides 10a-e were employed. Other factors such as solvent and amount of base also influenced the stereochemistry of this reaction. A mechanistic rationale is discussed briefly.
机译:由相应的碲盐1a-e原位生成的半稳定碲烷基化物2a-e与α,β-不饱和酮6a-d反应,得到具有高立体选择性和顺式的乙烯基-2-乙烯基-反式-3-取代的环丙基酮。产量高至优异。相反,当使用相应的砷化铵10a-e时,这些烯酮得到反式-2-乙烯基-反式-3-取代的环丙基酮。其他因素,例如溶剂和碱的量也影响该反应的立体化学。简要讨论了机械原理。

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