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Journal Article

Crystal structures of proline-derived enamines

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Bock,  Dominique Anna
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Bock, D. A., Lehmann, C. W., & List, B. (2010). Crystal structures of proline-derived enamines. Proceedings of the National Academy of Sciences of the United States of America, 107(48), 20636-20641. doi:10.1073/pnas.1006509107.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-8DC3-A
Abstract
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.