title: Diastereoselective synthesis of 2,3,5-trisubstituted tetrahydrofurans via cyclofunctionalization reactions. Evidence of stereoelectronic effects.
abstract: The work described herein considers the impact of stereoelectronic effects and allylic 1,3-strain in controlling the cyclofunctionalization reaction when a hydroxyl group is at the allylic position. The stereoelectronic arguments are supported by independent iodocyclization reactions performed using two secondary alcohols. The transition-state pathways involved in these reactions are established through a comparison of relative reaction rates. A bi-directional approach is used to demonstrate the potential of the iodocyclization reaction to differentiate a terminus in molecules with a pseudo C(2) axis of symmetry, showing that two-directional synthesis can be used to differentiate between alternative transition-state pathways.
authors.affiliation: Institut de recherches cliniques de Montréal (IRCM), Bio-organic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7. guindoy@ircm.qc.ca
authors.forename: Y
authors.initials: Y
authors.lastname: Guindon
authors.forename: F
authors.initials: F
authors.lastname: Soucy
authors.forename: C
authors.initials: C
authors.lastname: Yoakim
authors.forename: W W
authors.initials: WW
authors.lastname: Ogilvie
authors.forename: L
authors.initials: L
authors.lastname: Plamondon