Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 18, Pages 3329-3338Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000594
Keywords
amines; asymmetric catalysis; chlorination; enantioselectivity; beta-keto esters; organocatalysis
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Funding
- Spanish Ministry of Science and Innovation
- European Regional Development Fund [CTQ2008-00187/BQU]
- Government of Aragon [GA E-71]
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Highly modular chiral amino diol derivatives have been used as organocatalysts in the enantioselective alpha-chlorination of cyclic beta-keto esters. Optimization of the catalyst structure and the reaction conditions has allowed the synthesis of optically active alpha-chlorinated products with high enantioselectivities (up to 96% ee) using inexpensive commercially available N-chlorosuccinimide (NCS) as the chlorine source under mild conditions.
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