4.7 Article

Primary Amine-Thioureas based on tert-Butyl Esters of Natural Amino Acids as Organocatalysts for the Michael Reaction

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 9, Pages 1355-1362

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800812

Keywords

amino acids; Michael addition; nitroolefins; organocatalysis; thioureas

Funding

  1. European Social Fund and National Resources (EPEAEK II)

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A new class of primary amine-thioureas based on tert-butyl esters of (S)-alpha-amino acids and (1S,2S)-diphenylethylenediamine was synthesized and their activity as catalysts in Michael additions was evaluated. Derivatives based on di-tert-butyl aspartate and tert-butyl O-tert-butyl threoninate provided the product of the reaction between trans-beta-nitrostyrene and acetone in quantitative yield and high enantioselectivity (87-91% ee). All the thioureas based on tert-butyl esters of amino acids catalyzed the reaction of nitroolefins with acetophenone with high enantioselectivity (92-98% ee). Thus, low-cost, commercially available tert-butyl esters of natural amino acids are very important chiral building blocks for the construction of novel chiral thioureas able to catalyze asymmetric Michael additions with high enantioselectivity.

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