Journal
SCIENCE
Volume 351, Issue 6276, Pages 961-965Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aad0591
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Funding
- National Science Foundation [CHE-0953259]
- National Science Foundation
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464992] Funding Source: National Science Foundation
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Chiral acid catalysts are useful for the synthesis of enantioenriched small molecules, but the standard catalysts require laborious and expensive preparations. Here, we describe a chiral Bronsted acid prepared in one step from naturally occurring (-)-menthol and readily available 1,2,3,4,5-pentacarbomethoxycyclopentadiene. Aromatic stabilization serves as a key contributing factor to the potent acidity of the resulting compound, which is shown to catalyze both Mukaiyama-Mannich and oxocarbenium aldol reactions with high efficiency and enantioselectivity. Catalyst loadings as low as 0.01 mole percent and preparative scalability (25 grams) are demonstrated. Alternative amide catalysts are also shown to be promising platforms. In addition to proton catalysis, a chiral anion pathway is demonstrated to be viable with this catalyst system.
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