This work reports the synthesis of diarylmethane derivatives via gold-catalyzed (4 + 2)-annulations between alkynyl benzaldehydes and allenamides, followed by an aza-Claisen rearrangement. Deuterium labeling and crossover experiments have been performed to confirm this proposed mechanism. With racemic 3-substituted allenamides in a substrate ratio (1:1), we employ chiral gold catalysts to achieve a dynamic kinetic resolution to obtain enantioenriched diarylalkylmethane derivatives with high e.r. levels (up to 93:7).

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http://dx.doi.org/10.1021/acs.orglett.1c03963DOI Listing

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