1298016-22-4Relevant academic research and scientific papers
Rhodium-Catalyzed Stereoselective Intramolecular Tandem Reaction of Vinyloxiranes with Alkynes: Atom- and Step-Economical Synthesis of Multifunctional Mono-, Bi-, and Tricyclic Compounds
Feng, Jian-Jun,Zhang, Junliang
, p. 1533 - 1542 (2017)
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 chirality from readily available vinyloxiranes to the corresponding products provides a highly efficient and practical access to these chiral cyclic compounds.
An atom-economic synthesis of bicyclo[3.1.0]hexanes by rhodium N-heterocyclic carbene-catalyzed diastereoselective tandem hetero-[5 + 2] cycloaddition/claisen rearrangement reaction of vinylic oxiranes with alkynes
Feng, Jian-Jun,Zhang, Junliang
, p. 7304 - 7307 (2011/06/27)
The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5 + 2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific, and diastereoselective access to [3.1.0] bicyclic products has been developed.
