Efficient nitrogen ring-expansion process facilitated by in situ hemiketal formation. An asymmetric schmidt reaction

V Gracias, GL Milligan, J Aube

Index: Gracias, Vijaya; Milligan, Gregory L.; Aube, Jeffrey Journal of the American Chemical Society, 1995 , vol. 117, # 30 p. 8047 - 8048

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Citation Number: 65

Abstract

We recently reported an intramolecular version of the Schmidt reaction'in which hydrazoic acid was replaced by an alkyl azide connected to the reactive ketone. 2 This is an unusual example of intramolecularity because the analogous H+-promoted intermolecular reaction does not succeed at alL3 Given the potential utility of a general method for the intermolecular insertion of an N-alkyl group adjacent to a ketone, other conditions to effect ...