Novel selectfluor and deoxo-fluor-mediated rearrangements. New 5(6)-methyl and phenyl methanopyrrolidine alcohols and fluorides

Grant R Krow; Guoliang Lin; Keith P Moore; Andrew M Thomas; Charles DeBrosse; Charles W Ross 3rd; Harri G Ramjit

doi:10.1021/ol0494818

Novel selectfluor and deoxo-fluor-mediated rearrangements. New 5(6)-methyl and phenyl methanopyrrolidine alcohols and fluorides

Org Lett. 2004 May 13;6(10):1669-72. doi: 10.1021/ol0494818.

Authors

Grant R Krow¹, Guoliang Lin, Keith P Moore, Andrew M Thomas, Charles DeBrosse, Charles W Ross 3rd, Harri G Ramjit

Affiliation

¹ Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. [email protected]

PMID: 15128263
DOI: 10.1021/ol0494818

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).