期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 8, 页码 2862-2868出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b12146
关键词
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资金
- Leverhulme Trust [RPG-2015-232]
The Diels-Alder (DA) reaction is a cornerstone of synthesis, yet Nature does not use catalysts for intermolecular [4+2] cycloadditions. Attempts to create artificial Diels-Alderases have also met with limited success, plagued by product inhibition. Using a simple Pd2L4 capsule we now show DA catalysis that combines efficient turnover alongside enzyme-like hallmarks. This includes excellent activity (k(cat)/k(uncat) > 10(3)), selective transition-state stabilization comparable to the most proficient DA catalytic antibodies, and control over regio- and chemoselectivity that would otherwise be difficult to achieve using small-molecule catalysts. Unlike other catalytic approaches that use synthetic capsules, this method is not defined by entropic effects; instead multiple H-bonding interactions modulate reactivity, reminiscent of enzymatic action.
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