Preparation of α-imino aldehydes by [1,3]-rearrangements of O-alkenyl oximes
The synthesis of α-imino aldehydes has been achieved through the thermal [1,3]-rearrangement of O-alkenyl benzophenone oximes. A copper-mediated C-O bond coupling between benzophenone oxime and alkenyl boronic acids provides facile access to the required O-alkenyl oximes and a Horner-Wadsworth-Emmons olefination can be applied to the α-imino aldehyde products to give γ-imino-α,β-unsaturated esters. The scope of the method is described and mechanistic experiments are discussed.
Kontokosta, Dimitra,Mueller, Daniel S.,Wang, Heng-Yen,Anderson, Laura L.
p. 4830 - 4833
(2013/10/08)
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