title: Novel selectfluor and deoxo-fluor-mediated rearrangements. New 5(6)-methyl and phenyl methanopyrrolidine alcohols and fluorides.
abstract: Stereoselective syntheses of novel 5,6-difunctionalized-2-azabicyclo[2.1.1]hexanes containing 5-anti-fluoro or hydroxyl in one methano bridge and a variety of syn- or anti-chloro, fluoro, hydroxy, methyl, or phenyl substituents in the other methano bridge have been effected. Rearrangements of iodides to alcohols were initiated using Selectfluor. Rearrangement of alcohols to fluorides was initiated using Deoxo-Fluor. Ring opening of 2-azabicyclo[2.2.0]hex-5-ene exo-epoxide with organocopper reagents is regioselective at C(5).
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. grantkrow@aol.com
authors.forename: Grant R
authors.initials: GR
authors.lastname: Krow
authors.forename: Guoliang
authors.initials: G
authors.lastname: Lin
authors.forename: Keith P
authors.initials: KP
authors.lastname: Moore
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Thomas
authors.forename: Charles
authors.initials: C
authors.lastname: DeBrosse
authors.forename: Charles W
authors.initials: CW
authors.lastname: Ross
authors.forename: Harri G
authors.initials: HG
authors.lastname: Ramjit