The Electron Spin as a Chiral Reagent. (12th December 2019)

• Record Type: Journal Article
• Authors: Metzger, Tzuriel S.; Mishra, Suryakant; Bloom, Brian P.; Goren, Naama; Neubauer, Avner; Shmul, Guy; Wei, Jimeng; Yochelis, Shira; Tassinari, Francesco; Fontanesi, Claudio; Waldeck, David H.; Paltiel, Yossi; Naaman, Ron
• Is Part Of: Angewandte Chemie. Volume 132:Number 4(2020)
• Page Start: 1670
• Page End: 1675
• Publication Date: 2019-12-12
• Subjects: Chiralität -- Chiral-induzierte Spinselektivität -- Elektrochemie -- Enantioselektivität -- Spin; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201911400
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: We show that enantioselective reactions can be induced by the electron spin itself and that it is possible to replace a conventional enantiopure chemical reagent by spin‐polarized electrons that provide the chiral bias for enantioselective reactions. Three examples of enantioselective chemistry resulting from electron‐spin polarization are presented. One demonstrates the enantioselective association of a chiral molecule with an achiral self‐assembled monolayer film that is spin‐polarized, while the other two show that the chiral bias provided by the electron helicity can drive both reduction and oxidation in enantiospecific electrochemical reactions. In each case, the enantioselectivity does not result from enantiospecific interactions of the molecule with the ferromagnetic electrode but from the polarized spin that crosses the interface between the substrate and the molecule. Furthermore, the direction of the electron‐spin polarization defines the handedness of the enantioselectivity. This work demonstrates a new mechanism for realizing enantioselective chemistry. Abstract : Verdrehtes Elektron : Enantioselektive Reaktionen können durch den Elektronenspin induziert werden, der somit enantiomerenreine Reagenzien als Steuerer der Chiralität ersetzen kann. Drei Beispiele enantioselektiver Chemie in elektrochemischen Reaktionen, die aus der Polarisierung des Elektronenspins resultieren, werden vorgestellt. Die Richtung der Elektronenspin‐Polarisierung bestimmt zudem die Händigkeit der Enantioselektivität.