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Synthesis of epibatidine isomers: Reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene derivatives

✍ Scribed by Caroline D. Cox; John R. Malpass

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 806 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00675-4

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✦ Synopsis

The coupling of N-protected 2-azabicyclo[2.2.1]hept-5-enes and 2-chloro-5-iodopyridine under reductive Heck conditions gives approximately equal amounts of exo-5-and exo-6-(6'-chloro-3'-pyridyl)-2-azabicyclo-[2.2. I]heptanes. The ratio varies slightly under a range of conditions but both products are isolated in every case (and in the corresponding reaction with 3-iodopyridine) contrary to a recent report that only the 5-exo-isomers are formed.

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