Abstract

Combined forces: Theory and experiment are used together to determine the mechanism of primary amino acid catalyzed intermolecular aldol reactions. A six-membered chairlike structure is determined to be the transition state for the reaction between benzaldehyde and cyclohexanone catalyzed by (S)-alanine (see scheme), and a carboxylic acid catalyzed enamine mechanism is shown to be the most favorable reaction pathway. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z502388_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

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