Asymmetric Organocatalytic Formal [2 + 2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis

• DOI: 10.1021/ja211878x
• Publication Date: 2012-01-23T20:49:52Z
• Authors: Łukasz Albrecht; Gustav Dickmeiss; Fabio Cruz Acosta; Carles Rodríguez-...; Rebecca L. Davis; Karl Anker Jørgensen
• Keywords: Squaramide; Stereocenter; Cyclobutanes; Formal synthesis

A new concept in organocatalysis allowing for the construction of cyclobutanes with four contiguous stereocenters complete diastereo- and enantiomeric control by a formal [2 + 2]-cycloaddition is presented. The based on simultaneous dual activation α,β-unsaturated aldehydes nitroolefins amino- hydrogen-bonding catalysis, respectively. bifunctional squaramide-based aminocatalyst has been designed synthesized order to enable such an strategy. potential scope reaction are demonstrated, computational studies which account stereochemical outcome