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A variety of 5‐indo‐1‐yl pyran‐2‐ones with an N−C axis were prepared via a carbene‐catalyzed oxidative [3+3] annulation of indole‐1‐pyruvate esters and enals. Asymmetric construction of pyran‐2‐one ring from enals ensures the realization of this strategy. The resulting compounds were converted into axially chiral N‐arylindoles with an N−C axis via a cycloaddtion aromatization.
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