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Allenylidene Induced 1,2-Metalate Rearrangement of Indole-Boronates: Diastereoselective Access to Highly Substituted Indolines.

A process to achieve 1,2-metalate rearrangements of indole boronate as a way to access substituted indolines in high diastereoselectivities is presented. The reaction involves the generation of a Cu-allenylidene, which is sufficiently electrophilic to induce the 1,2-metalate rearrangement. The scope of the reaction is evaluated as well as further transformations of the product.