Acid-catalysed transformation of α-trifluoromethanesulfonates of γ- and δ-lactones into 2,5-disubstituted homochiral tetrahydrofurans
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 1065-1067
- https://doi.org/10.1039/c39930001065
Abstract
Excellent yields of methyl tetrahydrofuran-α-carboxylates are obtained by treatment of 2-O-trifluoromethanesulfonates (triflates) of either 1,4-or 1,5-lactones with acid in methanol; in some cases, very different tetrahydrofurans may result from acid or base treatment of a methanolic solution of the same starting material.Keywords
This publication has 16 references indexed in Scilit:
- 3-Hydroxymuscarines from L-RhamnoseTetrahedron, 1993
- Access toTetrahedron Letters, 1992
- Vicinal polyepoxides in biomimetic synthesis. Total synthesis of (±)-citreoviral and related substituted tetrahydrofuransTetrahedron Letters, 1992
- 3R-Hydroxymuscarine from L-rhamnose without protectionTetrahedron Letters, 1992
- Stereocontrolled formation of Polysubstitued tetrahydorfurans by debenzylating cycloetherificationTetrahedron Letters, 1992
- Iodocyclization of olefinic t-butyl ethers : an easy stereocontrolled synthesis of cis-substituted tetrahydrofurans.Tetrahedron Letters, 1992
- Development of tetrahydrofuran chiral synthons by enzymatic approach: Improved synthesis of a strong agonist of platelet activating factorTetrahedron Letters, 1992
- The ring contraction of δ-lactones with leaving group α-substituents: a strategy for the synthesis of 2,5-disubstituted highly functionalised homochiral tetrahydrofuransJournal of the Chemical Society, Chemical Communications, 1992
- A practical synthesis of (+)-muscarine from L-rhamnoseJournal of the Chemical Society, Perkin Transactions 1, 1992
- Stereoselective synthesis of 3-(phenylsulphonyl)-2,5 disubstituted tetrahydrofurans via 5-endo-trig ring-closure reactionsTetrahedron Letters, 1992