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Asymmetry by Electrophilic Rearrangement of Symmetric 2-Pyridone Photodimers

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posted on 24.11.2005, 00:00 authored by Yeon-Hee Lim, Tindy Li, Peiling Chen, Patrick Schreiber, Larissa Kuznetsova, Patrick J. Carroll, Joseph W. Lauher, Scott McN. Sieburth
Halogenation of achiral trans-2-pyridone photodimers results in 1,3-migration of an amide nitrogen and formation of a chiral structure with six stereogenic centers and well-differentiated functionality. The reactivity of this product toward nucleophiles, including the allylic halide, is dominated by participation by the amide nitrogen.