Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 5, Pages 2543-2546Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja211878x
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Funding
- Aarhus University
- FNU
- Carlsberg Foundation
- Generalitat de Catalunya for a Beatriu de Pinos postdoctoral fellowship
- CSIC
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A new concept in organocatalysis allowing for the construction of cyclobutanes with four contiguous stereocenters with complete diastereo- and enantiomeric control by a formal [2 + 2]-cycloaddition is presented. The concept is based on simultaneous dual activation of alpha,beta-unsaturated aldehydes and nitroolefins by amino- and hydrogen-bonding catalysis, respectively. A new bifunctional squaramide-based aminocatalyst has been designed and synthesized in order to enable such an activation strategy. The potential and scope of the reaction are demonstrated, and computational studies which account for the stereochemical outcome are presented.
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