Dynamic Spin-Controlled Enantioselective Catalytic Chiral Reactions

Tzuriel S. Metzger, Reema Siam, Yuval Kolodny, Naama Goren, Nir Sukenik, Shira Yochelis, Raed Abu-Reziq, David Avnir, Yossi Paltiel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Enantioselective catalytic chiral reactions are important to all aspects of life sciences. Here we present the first utilization of the chiral induced spin selectivity (CISS) effect to form, enantioselectively, sp3 chiral centers in catalytic reactions, starting from achiral reagents. The enantiomeric symmetry is broken by affecting spin-controlled different reaction dynamics toward each of the enantiomers, using magnetic substrates. Two catalytic reactions are used for this purpose: a sulfide to sulfoxide oxidation and a Diels-Alder cycloaddition reaction, both catalyzed by hematite (Fe2O3). The proof of concept was evaluated by circular dichroism measurements and by chiral high-performance liquid chromatography techniques. These results provide direct evidence that the directionality of the electron spin can break enantiomeric symmetry, enabling asymmetric catalysis without using chiral reagents, solvents, or catalysts.

Original languageAmerican English
Pages (from-to)5469-5472
Number of pages4
JournalJournal of Physical Chemistry Letters
Volume12
Issue number23
DOIs
StatePublished - 17 Jun 2021

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society.

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