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Stereodivergent Anion Binding Catalysis with Molecular Motors
Author(s) -
Dorel Ruth,
Feringa Ben L.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913054
Subject(s) - enantioselective synthesis , oxocarbenium , ketene , chemistry , nucleophile , chirality (physics) , isomerization , stereoselectivity , catalysis , supramolecular chemistry , silylation , molecular machine , stereochemistry , molecule , nanotechnology , organic chemistry , materials science , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
A photoresponsive chiral catalyst based on an oligotriazole‐functionalized unidirectional molecular motor has been developed for stereodivergent anion binding catalysis. The motor function controls the helical chirality of supramolecular assemblies with chloride anions, which by means of chirality transfer enables the enantioselective addition of a silyl ketene acetal nucleophile to oxocarbenium cations. Reversal of stereoselectivity (up to 142 % Δ ee ) was achieved through rotation of the motor core induced by photochemical and thermal isomerization steps.