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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Doi:10.1002/hlca.19970800811
(1997)Doi:10.1016/S0040-4039(97)10393-8
(1997)Doi:10.1039/a704416j
(1998)Doi:10.1021/jf60158a032
(1968)Doi:10.1016/S0957-4166(97)00588-0
(1997)Doi:10.1002/hlca.19680510503
(1968)