Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 7, Pages 1179-1184Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.201000982
Keywords
aldol reaction; esters; beta-hydroxy carbonyl compounds; ketones; organocatalysis
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Funding
- European Commision [FP7-201431 (CATA-FLU.OR)]
- PolyU Internal Grant DA [A-PD0X]
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This update describes a highly efficient organocatalytic aldol reaction of ketones and beta,gamma-unsaturated alpha-keto esters for constructing the chiral tertiary alcohol motif. With the application of 9-amino(9-deoxy)epi-Cinchona alkaloid and an acidic additive as catalysts, both acyclic and cyclic ketones react with beta,gamma-unsaturated alpha-keto esters smoothly to afford aldol adducts in good to excellent yields and asymmetric induction. This protocol offers a new pathway for the construction of adjacent chiral carbon centers and the synthesis of chiral beta-hydroxy carbonyl compounds.
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