Asymmetric Synthesis through C–H Activation

Davies, Huw M. L.; Hansen, Jørn H.

doi:10.1002/9780470584248.ch4

Cited by 12 publications

(1 citation statement)

References 280 publications

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“…Therefore, introducing highly sustainable and powerful methodologies for stereoselective C–C bond formations is strongly required. For this requirement, direct carbon–hydrogen (C–H) functionalization has received considerable attention and has been intensively studied because C–H bonds are ubiquitous and abundant in organic molecules and are tolerant under various reaction conditions. , Moreover, C–H functionalization can construct strategic high atom- and step-economic organic syntheses. Although various methodologies have been reported in this field, stereoselective C–C bond formation via C–H bond activation is still limited.…”

Section: Introductionmentioning

confidence: 99%

Iridium(III)-Catalyzed Asymmetric Site-Selective Carbene C–H Insertion during Late-Stage Transformation

et al. 2022

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C–H functionalization has recently received considerable attention because C–H functionalization during the late-stage transformation is a strong and useful tool for the modification of the bioactive compounds and the creation of new active molecules. Although a carbene transfer reaction can directly convert a C–H bond to the desired C–C bond in a stereoselective manner, its application in late-stage material transformation is limited. Here, we observed that the iridium–salen complex 6 exhibited efficient catalysis in asymmetric carbene C–H insertion reactions. Under optimized conditions, benzylic, allylic, and propargylic C–H bonds were converted to desired C–C bonds in an excellent stereoselective manner. Excellent regioselectivity was demonstrated in the reaction using not only simple substrate but also natural products, bearing multiple reaction sites. Moreover, based on the mechanistic studies, the iridium-catalyzed unique C–H insertion reaction involved rate-determining asynchronous concerted processes.

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Section: Introductionmentioning

confidence: 99%