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Crystal structures of proline-derived enamines.

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.

SUBMITTER: Bock DA 

PROVIDER: S-EPMC2996454 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Crystal structures of proline-derived enamines.

Bock Dominique Anna DA   Lehmann Christian W CW   List Benjamin B  

Proceedings of the National Academy of Sciences of the United States of America 20101110 48

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 postu  ...[more]

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