Conditions to harness the rearrangement reactivity of O-alkenyl oxime ethers have been determined and used to develop a unique method for the synthesis of a-amino aldehydes.  We have shown that these important synthetic intermediates can be prepared in a simple two-step process directly from alkenyl boronic acids, avoiding the use of electrophilic oxygenation reagents and eliminating the need for commercially available amino acids.  A mild, copper-mediated C�O bond coupling is used to form the required O-alkenyl oxime ethers.  The optimization, scope, and application of this new method to the synthesis of a-amino-a,�-unsaturated esters will be described and mechanistic studies will be discussed.

Preparation of a-imino aldehydes by [1,3]-rearrangement of <i>O</i>-alkenyl oximes

247th National Meeting (2014)

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Preparation of a-imino aldehydes by [1,3]-rearrangement of O-alkenyl oximes