Computational Evidence for the Enamine Mechanism of Intramolecular Aldol Reactions Catalyzed by Proline

✍ Scribed by Fernando R. Clemente; K. N. Houk

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 336 KB
• Volume: 43
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200460916

✦ Synopsis

Theoretical evidence now suggests that the mechanism of the longdebated Hajos-Parrish-Eder-Sauer-Wiechert reaction, the prototype for asymmetric organocatalytic reactions, involves a proline enamine intermediate (center) which undergoes a concerted aldol cyclization with proton transfer. For more details see the Communication by K. N. Houk and F. R. Clemente on the following pages.