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Cyclobutanes are regarded as synthetically useful intermediates due to their presence in natural products and bioactive molecules, and their prevalence as motifs in medicinal chemistry is increasing. Additionally, the strained rings can be easily functionalized to access ring-expanded or ring-opened products. Since organoboron compounds serve as versatile intermediates, the synthesis of cyclobutylboronates has been achieved to enable access to a diverse array of functionalized cyclobutanes. During the PhD research, boron-enabled [2+2] cycloaddition methods were developed to advance the synthesis of complex molecules. Using two different strategies, borylated cyclobutanes were synthesized from readily available alkenylboronates with either activated alkenes or allylic alcohols. Both methods have been demonstrated to be useful in the synthesis of natural products such as melicodenine C and artochamin J. In addition to simple cyclobutanes, a new approach to accessing synthetically challenging housanes was discovered. Lastly, boron was utilized as a tool to constrain bond rotation, which enabled triplet sensitization of the constrained alkene and enhanced the reactivity of inactivated alkenes in the [2+2]-cycloaddition. The products were obtained as cyclobutane-based glycols and/or 1,4-diketone compounds as a net result of alkene 1,2-diacylation.
- Liu, Y
- Department of Chemistry, Indiana University