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Please login to access the full content or check if you have access via Variation 1: From Ketones with Alkyl Azides

DOI: 10.1055/sos-SD-021-00115

Judd, W. R.; Katz, C. E.; Aubé, J.Science of Synthesis, (200521150.

Attempts to form the corresponding N-alkyl amides by reactions of alkyl azides under standard Schmidt conditions fail.[‌37‌,‌50‌] A notable exception is the reaction of aromatic aldehydes with alkyl azides, although this reaction occurs in only a very small number of cases to give modest product yields.[‌51‌] The use of Lewis acid activation instead of the protic conditions used in the standard Schmidt reaction permits a wider variety of alkyl azide mediated Schmidt reactions of a broader, but still limited, range of cyclic ketones (e.g., 49); an example is given in Scheme 22.[‌52‌,‌53‌]

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