Tetrahedron p. 16241 - 16252 (1997)
Update date:2022-08-04
Topics:
Gracias, Vijaya
Frank, Kristine E.
Milligan, Gregory L.
Aube, Jeffrey
Although alkyl azides can react with ketones to form ring- expanded lactams, the reaction suffers from poor generality and the need to use powerful Lewis acid promotion. The reactions of 1,2- and 1,3-hydroxyalkyl azides with ketones yield N-hydroxyalkyl lactams in high yields under the action of protic or Lewis acids such as BF3·OEt2. The reaction appears to succeed due to the initial formation of a hemiketal, which then renders the attack of azide on an oxonium ion intramolecular. The scope of this reaction vis a vis ketone and hydroxyalkyl azide structure is discussed.
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