%0 Generic %A Lim, Yeon-Hee %A Li, Tindy %A Chen, Peiling %A Schreiber, Patrick %A Kuznetsova, Larissa %A Carroll, Patrick J. %A Lauher, Joseph W. %A Sieburth, Scott McN. %D 2005 %T Asymmetry by Electrophilic Rearrangement of Symmetric 2-Pyridone Photodimers %U https://acs.figshare.com/articles/dataset/Asymmetry_by_Electrophilic_Rearrangement_of_Symmetric_2_Pyridone_Photodimers/3255484 %R 10.1021/ol052071e.s003 %2 https://acs.figshare.com/ndownloader/files/5090863 %K photodimer %K Electrophilic %K Symmetric %K stereogenic %K allylic %K reactivity %K Halogenation %K Asymmetry %K halide %K functionality %K amide nitrogen %K participation %K Pyridone %K achiral %K formation %K Rearrangement %K nucleophile %K center %K pyridone %K chiral %K tran %K Photodimer %K migration %X 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. %I ACS Publications