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Angew Chem Int Ed Engl. 2014 Jun 16;53(25):6468-72. doi: 10.1002/anie.201402233. Epub 2014 May 20.

Highly enantioselective carbonyl-ene reactions of 2,3-diketoesters: efficient and atom-economical process to functionalized chiral α-hydroxy-β-ketoesters.

Author information

1
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA).

Abstract

Carbonyl-ene reactions of 2,3-diketoesters catalyzed by [Cu{(S,S)-tBu-box}](SbF6)2 [box=bis(oxazoline)] generate chiral α-functionalized α-hydroxy-β-ketoesters in up to 94% yield and 97% ee. The 2,3-diketoesters are conveniently accessed from the corresponding α-diazo-β-ketoester, and a catalyst loading as low as 1.0 mol% can be achieved.

KEYWORDS:

asymmetric catalysis; carbonyl-ene reaction; copper; ligand effects; synthetic methods

PMID:
24846809
DOI:
10.1002/anie.201402233
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