Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 41, Pages 17743-17750Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c08639
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Funding
- Edinburgh Global Research Scholarship - AWE
- EPSRC Theory and Modelling in Chemical Sciences Doctoral Training Centre - AWE [EP/L015722/1]
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Carbon-carbon bond-forming processes that involve the deprotonation of a weakly acidic C-H pro-nucleophile using a strong Bronsted base are central to synthetic methodology. Enzymes also catalyze C-C bond formation from weakly C-H acidic substrates; however, they accomplish this at pH 7 using only collections of noncovalent interactions. Here, we show that a simple, bioinspired synthetic cage catalyzes Michael addition reactions using only Coulombic and other weak interactions to activate various pronucleophiles and electrophiles. The anion-stabilizing property of the cage promotes spontaneous pro-nucleophile deprotonation, suggesting acidity enhancement equivalent to several pK, units. Using a second noncovalent reagent-commercially available 18-crown-6-facilitates catalytic base-free addition of several challenging Michael partners. The cage's microenvironment also promotes high diastereoselectivity compared to a conventional base-catalyzed reaction.
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