Synthesis of cis- and trans-2,5-disubstituted tetrahydrofurans by a tandem dihydroxylation-SN2 cyclization sequence.
[reaction: see text] Dihydroxylation of delta- and epsilon-mesyloxy alpha,beta-unsaturated esters proceeds with in situ cyclization to afford 2,5-disubstituted and 2,3,5-trisubstituted tetrahydrofurans.
Marshall
James A
JA
Department of Chemistry, University of Virginia, Charlottesville, 22904, USA. jam5x@virginia.edu
Sabatini
Jesse J
JJ
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans