Chiral Amino Diol Derivatives as New Modular Organocatalysts for the Enantioselective α-Chlorination of Cyclic β-Keto Esters

Highly modular chiral amino diol derivatives have been used as organocatalysts in the enantioselective α‐chlorination of cyclic β‐keto esters. Optimization of the catalyst structure and the reaction conditions has allowed the synthesis of optically active α‐chlorinated products with high enantiosele...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2010-12, Vol.352 (18), p.3329-3338
Main Authors: Etayo, Pablo, Badorrey, Ramón, Díaz-de-Villegas, María D., Gálvez, José A.
Format: Article
Language:English
Subjects:
amines
asymmetric catalysis
chlorination
enantioselectivity
organocatalysis
β-keto esters
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Summary:Highly modular chiral amino diol derivatives have been used as organocatalysts in the enantioselective α‐chlorination of cyclic β‐keto esters. Optimization of the catalyst structure and the reaction conditions has allowed the synthesis of optically active α‐chlorinated products with high enantioselectivities (up to 96% ee) using inexpensive commercially available N‐chlorosuccinimide (NCS) as the chlorine source under mild conditions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201000594