%0 Journal Article %A Krow, Grant R. %A Lin, Guoliang %A Yu, Fang %A Sonnet, Philip E. %D 2003 %T Second-Chance Rearrangement Route to Novel 5(6)-Syn,anti-difunctional 2-Azabicyclo[2.1.1]hexanes %U https://acs.figshare.com/articles/journal_contribution/Second-Chance_Rearrangement_Route_to_Novel_5_6_-Syn_anti-difunctional_2-Azabicyclo_2_1_1_hexanes/3747597 %R 10.1021/ol0349662.s001 %2 https://acs.figshare.com/ndownloader/files/5840958 %K mercury salt enhancement %K Rearrangement %K regioselective additions %K Syn %K iodide nucleofugacity %K aziridinium ions %K Azabicyclo %K syn %K synthese %K endo %K iodo %K OH %K difunctionalized %K stereocontrolled manner %K exo %K hydroxy %K fluoro substituents %X The first syntheses of 5,6-difunctionalized-2-azabicyclo[2.1.1]hexanes containing syn-hydroxy and syn-fluoro substituents have been effected in a stereocontrolled manner. The key reactions are regioselective additions to the aziridinium ions formed from 6-exo-iodo(bromo)-5-endo-X-2-azabicyclo[2.2.0]hexanes (X = F, OH) upon silver or mercury salt enhancement of iodide nucleofugacity. %I ACS Publications