Preparation of α-Imino Aldehydes by [1,3]-Rearrangements of O-Alkenyl Oximes
Organic Letters2013Vol. 15(18), pp. 4830–4833
Citations Over TimeTop 22% of 2013 papers
Abstract
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.
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