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Remarkable Rate Enhancement of Ligand Substitution Promoted by Geometrical Arrangement of Tridentate "Spectator" Ligands K.J.T. acknowledges Arco Chemical and the National Science Foundation for support of this research. M.H.V.H. gratefully acknowledges postdoctoral fellowship support from the Director's Office of Los Alamos National Laboratory. Los Alamos National Laboratory is operated by the University of California for the U.S. Department of Energy under Contract W-7405-ENG-36. M.H.V.H. also thanks Dr. Beverly K. Hartline (Deputy Laboratory Director, Argonne National Laboratory), Dr. Donald G. Lee (Chemistry Professor, University of Regina, Saskatchewan, Canada, S4S0A2), Dr. R. Thomas Baker (Los Alamos National Laboratory), and Dr. David E. Morris (Los Alamos National Laboratory) for their suggestions and discussions.

Huynh, My Hang V.; Smyth, Jennifer; Wetzler, Modi; Mort, Brendan; Gong, Paul K.; Witham, Laura M.; Jameson, Donald L.; Geiger, David K.; Lasker, Joanne M.; Charepoo, Mina; Gornikiewicz, Michelle; Cintron, Jose M.; Imahori, Gretchen; Sanchez, Roberto R.; Marschilok, Amy C.; Krajkowski, Lynn M.; Churchill, David G.; Churchill, Melvyn Rowen; Takeuchi, Kenneth J..

Angew Chem Int Ed Engl ; 40(23): 4469-4473, 2001 Dec 03.

Article in English | MEDLINE | ID: mdl-12404448

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

Davies, Huw M. L.; Ahmed, Gulzar; Calvo, Rebecca L.; Churchill, Melvyn Rowen; Churchill, David G..

J Org Chem ; 63(8): 2641-2645, 1998 Apr 17.

Article in English | MEDLINE | ID: mdl-11672131

ABSTRACT

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.

ABSTRACT

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