Diastereoselective Rh-Mediated Construction of 2,3,5-Trisubstituted Tetrahydrofurans.
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.
Taber
Douglass F.
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716.
Song
Ying
Y