Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 36, Pages 15252-15258Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c07212
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Funding
- National Science Foundation [1828064, CHE-1856613]
- Program for Advancing Strategic International Networks to Accelerate the Circulation of Talented Researchers from the Japan Society for the Promotion of Science (JSPS) [R2801]
- University of Florida
- NIH [S10 OD021758-01A1]
- EU through the European Regional Development Fund (TK141 Advanced materials and high-technology devices for energy recuperation systems)
- Estonian Research Council [PRG690]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1828064] Funding Source: National Science Foundation
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Readily available 1,2-amino alcohols provide the framework for a new generation of chiral carboxylic acid catalysts that rival the acidity of the widely used chiral phosphoric acid catalyst (S)-TRIP. Covalently linked thiourea sites stabilize the carboxylate conjugate bases of these catalysts via anion-binding, an interaction that is largely responsible for the low pK(a) values. The utility of the new catalysts is illustrated in the context of challenging [4 + 2] cycloadditions of salicylaldehyde-derived acetals with homoallylic and bishomoallylic alcohols, providing polycyclic chromanes in a highly enantioselective fashion.
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