Albeit their utility, syntheses available to access optically active borocyclopropanes are limited. A one-step procedure to obtain enantioenriched bifunctional tetracoordinate cyclopropyl boronates via a non-oxidative work-up for the dioxaborolane-mediated cyclopropanation reaction has been established. Diethanolamine-promoted selective decomplexation of the dioxaborolane from the boron-ligated cyclopropylmethanol intermediate provides enantioenriched cyclopropyl boronates from their corresponding allylic alcohols. The synthetic utility of this methodology is demonstrated via Suzuki-Miyaura cross-couplings of CIDA borocyclopropanes with <i>N</i>-heterocycles offering a general methodology to access enantioenriched <i>N</i>-heterocycle substituted cyclopropanes from simple, solid and stable building blocks under mild conditions. A robustness test of various base-sensitive functionalities was implemented via Glorius’s rapid functional group assessment methodology which further enhances the scope for the dioxaborolane-mediated cyclopropanation reaction.

Access to enantioenriched bifunctional CIDA borocyclopropanes: A general solution to the dioxaborolane-mediated cyclopropanation of oxidation-prone and base-sensitive allylic alcohols

256th National Meeting (2018)

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