TY - JOUR
T1 - Dynamic Spin-Controlled Enantioselective Catalytic Chiral Reactions
AU - Metzger, Tzuriel S.
AU - Siam, Reema
AU - Kolodny, Yuval
AU - Goren, Naama
AU - Sukenik, Nir
AU - Yochelis, Shira
AU - Abu-Reziq, Raed
AU - Avnir, David
AU - Paltiel, Yossi
N1 - Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/6/17
Y1 - 2021/6/17
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85108386818&partnerID=8YFLogxK
U2 - 10.1021/acs.jpclett.1c01518
DO - 10.1021/acs.jpclett.1c01518
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C2 - 34085834
AN - SCOPUS:85108386818
SN - 1948-7185
VL - 12
SP - 5469
EP - 5472
JO - Journal of Physical Chemistry Letters
JF - Journal of Physical Chemistry Letters
IS - 23
ER -