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Issue 14, 2006
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Dual mechanism of zinc-proline catalyzed aldol reactions in water

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Abstract

The aldol reaction of acetone with aldehydes in aqueous medium under catalysis by zinc-proline (Zn(L-Pro)2) and secondary amines such as proline, (2S,4R)-4-hydroxyproline (Hyp) and (S)-(+)-1-(2-pyrrolidinomethyl)pyrrolidine (PMP) is shown to proceed by an enamine mechanism, as evidenced by reductive trapping of the iminium intermediate, while the aldol reaction of dihydroxyacetone (DHA) under catalysis by zinc-proline and by general bases such as N-methylmorpholine (NMM) is shown to occur under rate-limiting deprotonation of the α-carbon and formation of an enolate intermediate.

Graphical abstract: Dual mechanism of zinc-proline catalyzed aldol reactions in water

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Supplementary files

Article information


Submitted
18 Jan 2006
Accepted
14 Feb 2006
First published
02 Mar 2006

Chem. Commun., 2006, 1482-1484
Article type
Communication

Dual mechanism of zinc-proline catalyzed aldol reactions in water

J. Kofoed, T. Darbre and J. Reymond, Chem. Commun., 2006, 1482
DOI: 10.1039/B600703A

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