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Rhodium(I)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C–C bond cleavage: efficient access to trans-bicyclic compounds

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Abstract

We report a rhodium-catalyzed asymmetric formal intermolecular [4 + 2] cycloaddition reaction of 2-alkylenecyclobutanols with α,β-unsaturated cyclic ketones leading to synthetically useful trans-bicyclic molecules. Three consecutive stereogenic centers are formed in a highly enantio- and diastereoselective manner. Stepwise C–C bond cleavage and annulation are likely involved in the reaction pathway. Here, iPr-Duphos is the viable chiral ligand that promotes excellent enantio-control.

Graphical abstract: Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C–C bond cleavage: efficient access to trans-bicyclic compounds

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Publication details

The article was received on 06 Nov 2017, accepted on 02 Jan 2018 and first published on 08 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04784C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Rhodium(I)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C–C bond cleavage: efficient access to trans-bicyclic compounds

    X. Zheng, R. Guo, G. Zhang and D. Zhang, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04784C

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