Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 107, Issue 48, Pages 20636-20641Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1006509107
Keywords
enamine catalysis; mechanism; organocatalysis
Categories
Funding
- Max-Planck-Gesellschaft
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
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The isolation and structural characterization of both aldehyde-and ketone-derived proline enaminones are reported and discussed. Crystal structures of 10 proline enamines provide information on stereochemical aspects, i.e., double bond configuration and syn-vs. anti-positioning of the carboxylate relative to the enamine double bond. Furthermore, the obtained crystal structures are compared with the density functional theory-calculated structures of the ground and transition state and the postulated Seebach-Eschenmoser transition state.
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