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Near‐Enantiopure Trimerization of 9‐Ethynylphenanthrene on a Chiral Metal Surface
Author(s) -
Stolz Samuel,
Yakutovich Aliaksandr V.,
Prinz Jan,
Dienel Thomas,
Pignedoli Carlo A.,
Brune Harald,
Gröning Oliver,
Widmer Roland
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.202006844
Subject(s) - enantiopure drug , enantioselective synthesis , chirality (physics) , enantiomer , intermetallic , catalysis , combinatorial chemistry , chemistry , molecule , materials science , stereochemistry , organic chemistry , physics , chiral symmetry breaking , alloy , quantum mechanics , quark , nambu–jona lasinio model
Enantioselectivity in heterogeneous catalysis strongly depends on the chirality transfer between catalyst surface and all reactants, intermediates, and the product along the reaction pathway. Herein we report the first enantioselective on‐surface synthesis of molecular structures from an initial racemic mixture and without the need of enantiopure modifier molecules. The reaction consists of a trimerization via an unidentified bonding motif of prochiral 9‐ethynylphenanthrene (9‐EP) upon annealing to 500 K on the chiral Pd 3 ‐terminated PdGa{111} surfaces into essentially enantiopure, homochiral 9‐EP propellers. The observed behavior strongly contrasts the reaction of 9‐EP on the chiral Pd 1 ‐terminated PdGa{111} surfaces, where 9‐EP monomers that are in nearly enantiopure configuration, dimerize without enantiomeric excess. Our findings demonstrate strong chiral recognition and a significant ensemble effect in the PdGa system, hence highlighting the huge potential of chiral intermetallic compounds for enantioselective synthesis and underlining the importance to control the catalytically active sites at the atomic level.