title: Diastereoselective Rh-Mediated Construction of 2,3,5-Trisubstituted Tetrahydrofurans.
abstract: Dirhodium(II) carboxylate catalyzed cyclization of a series of gamma-alkoxy-alpha-diazo esters 1 has been shown to proceed with substantial diastereoselectivity, producing the 2,3,5-trisubstituted tetrahydrofurans 2 and 3. The diastereoselectivity of the cyclization improved as the electron-withdrawing ability of the substituent R increased. A mechanistic hypothesis is presented.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716.
authors.forename: Douglass F.
authors.initials: DF
authors.lastname: Taber
authors.forename: Ying
authors.initials: Y
authors.lastname: Song