Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 17, Pages 5868-5872Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600280
Keywords
asymmetric synthesis; enamines; enols; organocatalyst; reaction mechanisms
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
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Organocatalyzed Michael, Mannich, and aldol reactions of aldehydes or ketones, as nucleophiles, have triggered several discussions regarding their reaction mechanism. (H2O)-O-18 has been utilized to determine if the reaction proceeds through an enamine or enol mechanism by monitoring the ratio of O-18 incorporated into the final product. In this communication, we describe the risk of (H2O)-O-18 as an evaluation tool for this mechanistic investigation. We have demonstrated that exchange of O-16/O-18 occurs in the aldehyde or ketone starting material, caused by the presence of (H2O)-O-18 and amine catalysts, before the Michael, Mannich, and aldol reactions proceed. Because the newly generated O-18 starting aldehydes or ketones and O-16 water affect the incorporation ratio of O-18 in the final product, the use of (H2O)-O-18 would not be appropriate to distinguish the mechanism of these organocatalyzed reactions.
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