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Issue 3, 2009
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Organocatalysis by bimacrocyclic NHCs: unexpected formation of a cyclic hemiacetal instead of a γ-butyrolactone

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Abstract

Two bimacrocyclic imidazolinium salts of different size, precursors to respective NHCs (N-heterocyclic carbenes), were tested as precatalysts in the reaction of aromatic aldehydes or ketones with enals. The expected lactones were produced in most cases, but in the reaction of methyl 4-formylbenzoate with cinnamaldehyde, the larger bimacrocycle led to the formation of a cyclic hemiacetal, while the smaller bimacrocycle gave the anticipated lactone.

Graphical abstract: Organocatalysis by bimacrocyclic NHCs: unexpected formation of a cyclic hemiacetal instead of a γ-butyrolactone

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Article information


Submitted
10 Sep 2008
Accepted
14 Oct 2008
First published
10 Dec 2008

Org. Biomol. Chem., 2009,7, 553-556
Article type
Paper

Organocatalysis by bimacrocyclic NHCs: unexpected formation of a cyclic hemiacetal instead of a γ-butyrolactone

O. Winkelmann, C. Näther and U. Lüning, Org. Biomol. Chem., 2009, 7, 553
DOI: 10.1039/B815828B

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