Computational Prediction of One-Step Synthesis of Seven-membered Fused Rings by (5+2) Cycloaddition Utilising Cycloalkenes.

ABSTRACT: The (5+2) cycloaddition reaction utilising cycloalkenes is rare, although it is one of the most efficient methods of constructing seven-membered fused rings because of its high atom- and step-economy. In this study, we used quantum mechanical calculations to predict the plausibility of using the Rh-catalysed intermolecular (5+2) cycloaddition of 3-acyloxy-1,4-enynes and cycloalkenes to produce fused seven-membered carbocycles. The calculation results suggest a convenient, highly efficient and energetically practical approach. Strained cycloalkenes, such as cyclopropene, have been predicted to be active, and the desired bicyclic product should be favoured, accompanied by the formation of byproducts from rearrangement reactions. The energy barriers of the alkene insertion step were analysed

SUBMITTER: Zhou CC 

PROVIDER: S-EPMC4510518 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature