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Synthesis 2012; 44(15): 2455-2462
DOI: 10.1055/s-0031-1289811
DOI: 10.1055/s-0031-1289811
paper
Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid
Further Information
Publication History
Received: 20 February 2012
Accepted after revision: 14 May 2012
Publication Date:
29 June 2012 (online)
Abstract
Novel C 2-symmetric chiral bioxazolines were synthesized in good yields by the fusion of optically active acids with a tartaric acid derivative. Complexes of these products with copper(II) acetate monohydrate were found to be excellent catalysts for the Henry reaction, giving various nitro alcohols in very good yields and up to 84% enantiomeric excess. Although only five-membered chelation is possible with these ligands, they give better enantioselectivities than other bioxazoline ligands that undergo similar coordination.
Key words
asymmetric catalysis - aldol reactions - heterocyclic compounds - nitro compounds - alcoholsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For recent reports on asymmetric Henry reactions, see: