Hydrophobic chirality amplification in confined water cages

Nature Communications
Choong Eui SongJi Yoon Jung

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.

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Citations

Feb 15, 2020·Chemistry : a European Journal·Taku Kitanosono, Shū Kobayashi
Dec 22, 2020·Chemical Communications : Chem Comm·Gabriela Oksdath-MansillaColin L Raston
Jan 14, 2021·Journal of the American Chemical Society·Si Joon ParkChoong Eui Song
Jan 20, 2021·Chemical Reviews·Thomas BuhseJean-Claude Micheau
Jun 4, 2021·ACS Central Science·Taku Kitanosono, Shu Kobayashi
Jun 18, 2021·The Journal of Physical Chemistry Letters·Wenxin WangJie Jiang
Aug 14, 2020·Journal of Chemical Theory and Computation·Kaihang ShiKeith E Gubbins
Oct 16, 2021·ACS Nano·Donglin LiWei Xu
Jan 12, 2022·The Journal of Physical Chemistry Letters·Yun JuJie Jiang

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Methods Mentioned

BETA
chip
column chromatography
NMR

Software Mentioned

ChemBioDraw Ultra

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