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- W2933901293 abstract "Abstract Deracemization is a powerful method by which a racemic mixture can be transformed into an excess of one enantiomer with the aid of chiral auxiliaries, but has been applied only to small chiral molecular systems. Here we report a deracemization of a racemic double-stranded spiroborate helicate containing a bisporphyrin unit upon encapsulation of chiral aromatic guests between the bisporphyrin. The chiral guest-included helicate is kinetically stable, existing as a mixture of right- and left-handed double helices, which eventually undergo an inversion of the helicity triggered by water resulting from the water-mediated reversible diastereoselective B-O bond cleavage/reformation of the spiroborate groups, thus producing an optically-active helicate with a high enantioselectivity. Quantum chemical calculations suggest that the stereospecific CH-π interactions between the porphyrin hydrogen atoms of the helicate and an aromatic pendant group of the chiral guest play a key role in the enhancement of the helical handedness of the helicate." @default.
- W2933901293 created "2019-04-11" @default.
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- W2933901293 date "2019-03-29" @default.
- W2933901293 modified "2023-10-01" @default.
- W2933901293 title "Water-mediated deracemization of a bisporphyrin helicate assisted by diastereoselective encapsulation of chiral guests" @default.
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- W2933901293 doi "https://doi.org/10.1038/s41467-019-09443-z" @default.
- W2933901293 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6441078" @default.
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