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Planar chiral [2.2]paracyclophane-based phosphine–phenols: use in enantioselective [3 + 2] annulations of allenoates and N-tosylimines

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Abstract

Planar chiral [2.2]paracyclophane-based phosphine–phenol catalysts, which have a benzene ring spacer inserted between the pseudo-ortho-substituted [2.2]paracyclophanol skeleton and the diarylphosphino group, are highly suitable for enantioselective [3 + 2] annulations of allenoates and N-tosylimines. These catalysts can be tuned by changing the substituent on the benzene rings of the diarylphosphino group. The observed enantioselectivity of 92% is the highest reported to date for phosphine-catalyzed annulations of unsubstituted allenic esters and N-tosylaldimines.

Graphical abstract: Planar chiral [2.2]paracyclophane-based phosphine–phenols: use in enantioselective [3 + 2] annulations of allenoates and N-tosylimines

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Publication details

The article was received on 30 Jan 2018, accepted on 14 Feb 2018 and first published on 14 Feb 2018


Article type: Paper
DOI: 10.1039/C8OB00248G
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Planar chiral [2.2]paracyclophane-based phosphine–phenols: use in enantioselective [3 + 2] annulations of allenoates and N-tosylimines

    S. Kitagaki, K. Nakamura, C. Kawabata, A. Ishikawa, N. Takenaga and K. Yoshida, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00248G

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