A versatile stereocontrolled approach to chiral tetrahydrofuran and tetrahydropyran derivatives via sequential asymmetric Horner-Wadsworth-Emmons and palladium-catalyzed ring closure reactions
[reaction: see text]An approach to chiral tetrahydrofuran and tetrahydropyran derivatives is reported which is based on the sequential use of an asymmetric Horner-Wadsworth-Emmons desymmetrization of a meso-dialdehyde and a palladium-catalyzed intramolecular allylic substitution. The strategy is versatile in that either a cis- or a trans-relation between the stereocenters adjacent to the ring oxygen can be obtained.
Vares
L
Department of Organic Chemistry, Kemitorvet, Technical University of Denmark, Kgs. Lyngby.
Rein
T