ChemInform Abstract: Stereoselective Synthesis of 2,3,4‐Trisubstituted Tetrahydrofurans.

Abstract

Stereoselective Synthesis of 2,3,4-Trisubstituted Tetrahydrofurans.-Treatment of the protected α-alkyl hydroxyaldehydes (I) and (IV) with the diazoacetates (II) in the presence of a Lewis acid forms the corresponding trisubstituted tetrahydrofurans stereoselectively. In general, triethylsilyl-protected derivatives (IV) afford higher yields of the tetrahydrofuran product. In addition, stereoselectivity increases with steric bulk of the α-alkyl substituent.-(ANGLE, S. R.; BERNIER, D. S.; CHANN, K.; JONES, D. E.; KIM, M.; NEITZEL, M. L.; WHITE, S. L.; Tetrahedron Lett. 39 (1998) 45, 8195-8198; Dep. Chem., Univ. Calif., Riverside, CA 92521, USA; EN)