Computational analyses have revealed that the distortion of a catalyst and the substrates and their interactions are key to determining the stability of the transition state. Hence, two strategies "distortion strategy" and "interaction strategy" can be proposed for improving enantiomeric excess in enantioselective reactions. The "distortion strategy" is used as a conventional approach that destabilizes the TS (transition state) of the minor pathway. On the other hand, the "interaction strategy" focuses on the stabilization of the TS of the major pathway in which an enhancement of the reaction rate is expected. To realize this strategy, we envisioned the TS stabilization of the major reaction pathway by reinforcing hydrogen bonding and adopted the chiral phosphoric acid-catalysed enantioselective Diels-Alder reaction of 2-vinylquinolines with dienylcarbamates. The intended "interaction strategy" led to remarkable improvements in the enantioselectivity and reaction rate.
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| http://dx.doi.org/10.1039/d3sc01637d | DOI Listing |
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