期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 41, 页码 13525-13528出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b09205
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资金
- NIH [GM-43214]
- NSF [DGE1144152]
- NSERC PDF
- Boehringer Ingelheim
- Eli Lilly
We describe the rational design of a linked, bis-thiourea catalyst with enhanced activity relative to monomeric analogues in a representative enantioselective anion-abstraction reaction. Mechanistic insights guide development of this linking strategy to favor substrate activation though the intramolecular cooperation of two thiourea subunits while avoiding nonproductive aggregation. The resulting catalyst platform overcomes many of the practical limitations that have plagued hydrogen-bond donor catalysis and enables use of catalyst loadings as low as 0.05 mol %. Computational analyses of possible anion binding modes provide detailed insight into the precise mechanism of anion-abstraction catalysis with this pseudo-dimeric thiourea.
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