Second-chance rearrangement route to novel 5(6)-syn,anti-difunctional 2-azabicyclo[2.1.1]hexanes.
[reaction: see text] 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.
Krow
Grant R
GR
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. grantkrow@aol.com
Lin
Guoliang
G
Yu
Fang
F
Sonnet
Philip E
PE