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

[reaction: see text] The reaction of alkyl azides with triethyl(1-methoxy-2, 2-dimethyl-cyclopropoxy)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).