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ChemInform Abstract: Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles.

โœ Scribed by H. M. L. DAVIES; J. J. MATASI; L. M. HODGES; N. J. S. HUBY; C. THORNLEY; N. KONG; J. H. HOUSER

Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
28
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Enantioselective

Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles. -A number of enantiomerically enriched tropones can be prepared efficiently using the title method. The reaction proceeds via a tandem cyclopropanation/Cope rearrangement. Best results are obtained using either (S)-lactate or (R)-pantolactone as chiral auxiliary on the vinyldiazomethanes. In the presence of a chiral catalyst moderate asymmetric induction as well as formation of side products are observed. This process is applied to the synthesis of (-)-anhydroecgonine methyl ester (VI) and (-)-ferruginine (VII). -(DAVIES, H.

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