Synthesis of endo-(3-azabicyclo[3.1.0]hex-6-yl)-methanol and derivatives as new geometric/charge mimics of glycosyltransfer transition states

The syntheses of azabicyclo[3.1.0]hexane transition state (TS) analogs are described. Cyclopropanation of N-Boc-3-pyrroline with ethyl diazoacetate afforded a 1.6:1 exo/endo ratio of the resulting ester. Reduction of the endo-isomer with LiAlH4 yielded the alcohol which was phosphorylated, or iodinated to provide access to aglycon containing TS analogs.