The influence of pentafluorosulfanylation on biological activity has been revealed in numerous comparative studies of biologically active compounds, but considerably less is known about the influence of pentafluorosulfanylation on reactivity. Among the distinctive properties of the pentafluorosulfanyl group is the profound dipole moment that results from introduction of this substituent. It has been shown that dipolar effects coupled with the steric demand of the SF₅ group may be employed to influence the stereochemistry of reactions, especially those processes with significant charge separation in the transition state. The Staudinger ketene-imine cycloaddition reaction is an ideal platform for investigation of dipolar control of diastereoselectivity by the pentafluorosulfanyl group.

中文翻译：

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五氟硫烷基对立体化学的控制†

在许多对生物活性化合物的比较研究中已经揭示了五氟磺酰化对生物活性的影响，但对五氟磺酰化对反应性的影响知之甚少。五氟硫烷基的独特特性之一是引入该取代基后产生的深刻偶极矩。已经表明，偶极效应与SF ₅基团的空间需求结合可以用来影响反应的立体化学，特别是那些在过渡态中具有明显电荷分离的过程。Staudinger烯酮-亚胺环加成反应是研究通过五氟硫烷基偶极控制非对映选择性的理想平台。