Asymmetry by Electrophilic Rearrangement of Symmetric 2-Pyridone Photodimers

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...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-11, Vol.7 (24), p.5413-5415
Main Authors: Lim, Yeon-Hee, Li, Tindy, Chen, Peiling, Schreiber, Patrick, Kuznetsova, Larissa, Carroll, Patrick J, Lauher, Joseph W, Sieburth, Scott McN
Format: Article
Language:English
Subjects:
Amides - chemistry
Hydrocarbons, Chlorinated - chemistry
Molecular Structure
Photochemistry
Pyridones - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052071e