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Second-Chance Rearrangement Route to Novel 5(6)-Syn,anti-difunctional 2-Azabicyclo[2.1.1]hexanes

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journal contribution
posted on 01.07.2003 by Grant R. Krow, Guoliang Lin, Fang Yu, Philip E. Sonnet
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.