Journal
ORGANIC LETTERS
Volume 12, Issue 10, Pages 2198-2201Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100493v
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Funding
- NSERC Canada
- Graduiertenschule Chemical Biology Konstanz
- Studienstiftung des Deutschen Volkes (German National Academic Foundation)
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A general and efficient directed ortho metalation (DoM)-halogen dance (HD)-electrophile quench sequence for the synthesis of trisubstituted pyridyl O-carbamates is described. A second HD sequence furnishes highly functionalized tetrasubstituted pyridines. Furthermore, a hitherto unobserved double HD rearrangement is reported. Under similar LDA conditions, aromatic O-carbamates with OMe, Cl, and F substituents (4a-c) undergo either a HD-electrophile quench sequence, 4a-c -> 18-20, or a HD-anionic ortho Fries rearrangement, 4a-c -> 6a-c, respectively.
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