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The tricyclo[2.1.0.02,5]pentan-3-one system: a new probe for the study of π-facial selectivity in nucleophilic additions
Tetrahedron Letters ( IF 1.5 ) Pub Date : 7 April 2003 , DOI: 10.1016/s0040-4039(03)00515-x Goverdhan Mehta , S.Robindro Singh , U.Deva Priyakumar , G.Narahari Sastry
Tetrahedron Letters ( IF 1.5 ) Pub Date : 7 April 2003 , DOI: 10.1016/s0040-4039(03)00515-x Goverdhan Mehta , S.Robindro Singh , U.Deva Priyakumar , G.Narahari Sastry
Monosubstituted tricyclo[2.1.0.02,5]pentan-3-one derivatives have been synthesised and subjected to hydride reduction. Quite unexpectedly and in contrast to earlier observations in related systems, anti-selectivity has been encountered in these substrates. Computational studies employing various models reproduce the observed facial preference and indicate that the causative factor for the anti-preference could be the polarization of the C1C5 strained σ bond.
中文翻译:
三环[2.1.0.0 2,5 ] pentan-3-one系统:研究亲核加成中的π面选择性的新探针
已经合成了单取代的三环[2.1.0.0 2,5 ]戊丹-3-酮衍生物并将其还原为氢化物。出乎意料的是,与相关系统中的早期观察结果相反,在这些底物中遇到了抗选择性。使用各种模型进行的计算研究重现了观察到的面部偏爱,并表明反偏爱的原因可能是C1C5应变σ键的极化。
更新日期:2017-01-31
中文翻译:
三环[2.1.0.0 2,5 ] pentan-3-one系统:研究亲核加成中的π面选择性的新探针
已经合成了单取代的三环[2.1.0.0 2,5 ]戊丹-3-酮衍生物并将其还原为氢化物。出乎意料的是,与相关系统中的早期观察结果相反,在这些底物中遇到了抗选择性。使用各种模型进行的计算研究重现了观察到的面部偏爱,并表明反偏爱的原因可能是C1C5应变σ键的极化。