%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