4.6 Article

Enantioselective direct aldol reaction of α-keto esters catalyzed by (Sa)-binam-D-prolinamide under quasi solvent-free conditions

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 20, Pages 4029-4035

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25224d

Keywords

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Funding

  1. Ministerio de Ciencia e Innovacion (MICINN) [CTQ2007-62771/BQU, CTQ2010-20387, CSD2007-00006]
  2. Generalitat Valenciana [PROMETEO/2009/039]
  3. EU (ORCA) [CM0905]
  4. Spanish MICINN [FPU AP2009-3601]

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(S-a)-Binam-D-prolinamide (20 mol%), instead of (S-a)-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between alpha-keto esters as electrophiles and alkyl and alpha-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary gamma-keto alpha-hydroxyesters with up to 92% ee.

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