STEREOSELECTIVE SYNTHESIS OF TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS VIA THE LEWIS ACID MEDIATED REDUCTION OF CYCLIC HEMIKETALS WITH TRIPHENYLSILANE

摘要

An efficient method for the synthesis of trans-2,5-disubstituted tetrahydrofuran derivatives has been developed. Dithioacetal-functionalized cyclic hemiketals are reduced by triphenylsilane (Ph(3)SiH) in the presence of TiCl4 to afford the corresponding trans-2,5-disubstituted tetrahydrofuran derivatives in good yield and high stereoselectivity. Asymmetrical synthesis of (2S,5S) disubstituted tetrahydrofuran was also achieved by using this reduction method. [References: 19]