Abstract
The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity. In particular, transition states of chemical reactions can be significantly modified in a confined environment. We report a catalytic reaction with remarkable amplification of stereochemical information in a confined water cage. Surprisingly, this amplification is significantly dependent on droplet size. This water-induced chirality amplification stems from the hydrophobic hydration effects, which ensures high proximity of the catalyst and substrates presumably at the transition state, leading to higher enantioselectivity. Flow and batch reactors were evaluated to confirm the generality of this water-induced chirality amplification. Our observation on efficient chiral induction in confined water cages might lead to an understanding of the chirality amplification in the prebiotic era, which is a key feature for the chemical evolution of homochirality.
Highlights
The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity
In summary, we demonstrated that water can induce the chirality amplification in a catalytic asymmetric reaction
Under on-water conditions, the enantioselectivity of a catalytic reaction can be significantly enhanced in the confined hydrophobic spaces of organic droplets surrounded by water
Summary
The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity. We report a catalytic reaction with remarkable amplification of stereochemical information in a confined water cage This amplification is significantly dependent on droplet size. This water-induced chirality amplification stems from the hydrophobic hydration effects, which ensures high proximity of the catalyst and substrates presumably at the transition state, leading to higher enantioselectivity. In a confined water cage, a hydrophobic catalyst and non-polar substrates would be brought together in a close proximity, constructing sterically more confined transition states, leading to higher stereoselectivities of asymmetric catalysis. We report our finding that, under on-water conditions, enantioselectivities of a catalytic reaction can be dramatically amplified in the confined hydrophobic cavities of microdroplets surrounded by hydration shell. The effect of the droplet size on the enantioselectivity was quantified by using the biphasic microfluidic technique
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