72. Asymmetric Synthesis of 2,3-Dihydrofurans by Reaction of Rhodium-Stabilized Vinylcarbenoids with Vinyl Ethers

Authors: Huw M. L. Davies , Gulzar Ahmed , Rebecca L. Calvo , Melvyn Rowen Churchill , and David G. Churchill

J. Org. Chem.,

1998, 63 (8), 2641–2645

Rhodium(II) octanoate catalyzed decomposition of 2-diazo-3-siloxybutenoates, containing (R)-pantolactone as a chiral auxiliary, in the presence of vinyl ethers results in the diastereoselective synthesis of cyclopropanes with high asymmetric induction. Treatment of the cyclopropanes with tetrabutylammonium fluoride results in desilylation and ring expansion of the resulting acylcyclopropanes to 2,3-dihydrofurans with retention of stereochemistry.

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