Abstract
Organic Chemistry Manipulation of carbon–nitrogen rings is integral to the synthesis of numerous pharmaceutical and agrochemical compounds. Jurczyk et al. report that photoexcitation of carbonyl-substituted cyclic amines can shift the nitrogen from inside to outside the ring framework. The reaction appears to proceed through a 1,5-hydrogen shift to the electronically excited carbonyl, which sets in motion the subsequent carbon–nitrogen and carbon–carbon bonding rearrangements. Several oxygen and sulfur heterocycles were applicable as well. Addition of a chiral phosphoric acid catalyst rendered the reaction asymmetric. Science , abi7183, this issue p. [1004][1] [1]: /lookup/doi/10.1126/science.abi7183
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