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Issue 18, 2018
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Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2] cycloaddition of 1,3-disubstituted allene-1,3-dienes

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Abstract

RhCl(PPh3)3-catalyzed [4 + 2] intramolecular cycloaddition of allene-1,3-dienes afforded cis-fused [3.4.0]-bicyclic products with three chiral centers in good yields with excellent chemo- and diastereoselectivity. The configuration of the C[double bond, length as m-dash]C bonds in the 1,3-diene unit controls the relative configurations of the non-bridging tertiary carbon atom in the six-membered ring. Based on the experimental results, a mechanism involving cyclometalation has been proposed.

Graphical abstract: Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2] cycloaddition of 1,3-disubstituted allene-1,3-dienes

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Publication details

The article was received on 02 Jul 2018, accepted on 27 Jul 2018 and first published on 31 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00650D
Citation: Org. Chem. Front., 2018,5, 2680-2684
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    Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2] cycloaddition of 1,3-disubstituted allene-1,3-dienes

    Y. Han and S. Ma, Org. Chem. Front., 2018, 5, 2680
    DOI: 10.1039/C8QO00650D

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