4.7 Article

Enantioselective Electrophilic Amination of α-Cyanothioacetates with Azodicarboxylates Catalyzed by an Axially Chiral Guanidine Base

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 17, Pages 2817-2821

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900594

Keywords

amination; amino acids; asymmetric catalysis; organocatalysis; quaternary stereocenters

Funding

  1. MEXT, Japan [19020006]
  2. JSPS Research Fellowship
  3. Grants-in-Aid for Scientific Research [19020006] Funding Source: KAKEN

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An enantioselective electrophilic amination of alpha-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Bronsted base catalyst. The corresponding product, having a quaternary stereogenic center at the alpha-carbon atom, is formed in excellent enantioselectivity.

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