PRODUCTION OF 2,3,5-TRISUBSTITUTED TETRAHYDROFURAN

摘要

PURPOSE:To obtain the titled compound useful as a synthetic unit for organic compounds, etc., by a simple operation in a short process in high yield in high selectively and in a large amount, by reacting a specific compound with a hydrosilane compound in the presence of Lewis acid catalyst in an organic solvent. CONSTITUTION:A compound shown by formula I (R1-R3 are alkyl, aryl or aralkyl; X is H or trialkylsilyl) is reacted with a hydrosilane compound shown by formula II (R4-R6 are H, alkyl or aryl) in an organic solvent such as methylene chloride, etc., in the presence of Lewis acid catalyst such as chlorotrimethylsilane, etc., at -20-25 deg.C for 0.1-2hr to give the aimed compound shown by formula III (relative steric configuration of carbon shown by * is different depending upon R3 and is alpha or beta). EFFECT:The aimed compound can be stereoselectively synthesized. The compound has thermodynamically unstable 2,5-cis relative steric configuration and a carbonyl group capable of undergoing carbon chain extension at the 3-position. The relative steric configuration can be expected.