Asymmetry by electrophilic rearrangement of symmetric 2-pyridone photodimers.
[reaction: see text] 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.
Lim
Yeon-Hee
YH
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794, USA.
Li
Tindy
T
Chen
Peiling
P
Schreiber
Patrick
P
Kuznetsova
Larissa
L
Carroll
Patrick J
PJ
Lauher
Joseph W
JW
Sieburth
Scott McN
SM
D000577:Amides / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D006843:Hydrocarbons, Chlorinated; D011728:Pyridones