Asymmetric Synthesis of 2,3-Dihydrofurans by Reaction of Rhodium-Stabilized Vinylcarbenoids with Vinyl Ethers.
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.
Davies
Huw M. L.
HM
Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260-3000.
Ahmed
Gulzar
G
Calvo
Rebecca L.
RL
Churchill
Melvyn Rowen
MR
Churchill
David G.
DG