Tetrahedron Letters p. 2303 - 2306 (1984)
Update date:2022-08-05
Topics:
Gilbert, John C.
Senaratne, K. P. A.
Base-promoted reaction of ketones and diethyl (diazomethyl)phosphonate in the presence of allylic amines affords allylic enamines in good yields.These enamines undergo <3,3>-sigmatropic rearrangement upon alkylation and heating at 80 deg C to iminium salts which can be hydrolyzed to aldehydes.The procedure allows generation of quaternary carbon centers under mild reaction conditions.
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Doi:10.1021/ja00336a003
(1984)Doi:10.1002/chem.200600332
(2006)Doi:10.1016/j.tet.2006.11.042
(2007)Doi:10.1021/om0607144
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(2016)
