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 α,β-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.
We describe accommodations that we have made to our applied
computational–theoretical
chemistry laboratory to provide access for blind and visually impaired
students interested in independent investigation of structure–function
relationships. Our approach utilizes tactile drawings, molecular model
kits, existing software, Bash and Perl scripts written in-house, and
three-dimensional printing in a process that allows a blind or visually
impaired student to satisfy her or his curiosity about structure–function
relationships with minimal assistance from sighted co-workers.
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