Water-mediated deracemization of a bisporphyrin helicate assisted by diastereoselective encapsulation of chiral guests

Naoki Ousaka, Shinya Yamamoto, Hiroki Iida, Takuya Iwata, Shingo Ito, Yuh Hijikata, Stephan Irle and Eiji Yashima ()
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Naoki Ousaka: Nagoya University
Shinya Yamamoto: Nagoya University
Hiroki Iida: Nagoya University
Takuya Iwata: Nagoya University
Shingo Ito: Nagoya University
Yuh Hijikata: Nagoya University
Stephan Irle: Nagoya University
Eiji Yashima: Nagoya University

Nature Communications, 2019, vol. 10, issue 1, 1-11

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.

Date: 2019
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DOI: 10.1038/s41467-019-09443-z

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