4.7 Article

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

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 5, Issue 18, Pages 2680-2684

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo00650d

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Funding

  1. National Natural Science Foundation of China [21690063]

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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?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.

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