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ChemInform Abstract: Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (.+-.)-Epibatidine and Analogues.

✍ Scribed by Andreas Palmgren; Anna L. E. Larsson; Jan-E. Baeckvall; Paul Helquist

Publisher
John Wiley and Sons
Year
2010
Weight
37 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (Β±)-Epibatidine and Analogues.

-1,4-Chloroacetoxylation of arenes (I) in the presence of palladium(II) catalyst gives cis-cyclohexenes (III) with high regio-and stereoselectivity. These products are applied in the stereoselective synthesis of the alkaloid epibatidine (XI) and the exo-and endo phenyl analogues (X) and (XV). - (PALMGREN,

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