Portal de Periódicos da CAPES

Reevaluation of the Mechanism of the Baylis–Hillman Reaction: Implications for Asymmetric Catalysis

2005; Wiley; Volume: 44; Issue: 11 Linguagem: Inglês

10.1002/anie.200462462

1521-3773

Varinder K. Aggarwal, Sarah Y. Fulford, Guy C. Lloyd‐Jones,

Organic Chemistry Cycloaddition Reactions

One step beyond: Proton transfer (step 3, see scheme), not CC bond formation (step 2) as previously thought, is the rate-limiting step (RLS) in the initial stage of the Baylis–Hillman reaction, which involves the amine-catalyzed addition of an aldehyde to an activated alkene to generate an allylic alcohol. This finding has considerable implications for asymmetric catalysis of the reaction. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z462462_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.