Synthesis of α-amino-α′-diazomethyl ketones via ring opening of substituted cyclopropanones with alkyl azides.: A facile route to N-substituted 3-azetidinones

[GRAPHICS] The reaction of alkyl azides with triethyl(1-methoxy-2,2-dimethyl-cycloproxy)silane affords a series of alpha-amino-alpha'-diazomethyl ketones in moderate yields (38-54%). The mechanism of this novel process is discussed, The diazomethyl ketones could also be cyclized to the corresponding N-substituted 3-azetidinones in good yield upon treatment with Rh-2(OAc)(4).