Abstract
Skeletal diversity in diversity-oriented synthesis has proven to be especially challenging. A rhodium-catalyzed intramolecular tandem reaction of vinyloxirane-alkynes leading to four structurally distinct classes of mono-, bi-, and tricyclic carbocycles and heterocycles was developed. [Rh(NBD)2]+BF4– is identified to be an efficient catalyst for these transformations. Using this highly efficient catalyst, hetero-[5 + 2] cycloadditions, tandem hetero-[5 + 2] cycloaddition/Claisen rearrangements, and subsequent cyclopropane ring-opening reactions of vinyloxiranes with monoalkynes afford 2,5-dihydrooxepins, tetrasubstituted vinylcyclopropanes, and multifunctional five-membered rings, respectively, under mild conditions with high stereoselectivity and yield. Moreover, hetero-[5 + 2] cycloaddition/Claisen rearrangement/[5 + 2] cycloaddition reactions of vinyloxiranes with diynes for step-economical construction of linearly fused 5-7-5 tricyclic skeletons has also been developed. The complete transfer of chiral...
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