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Asymmetric Autocatalysis: Triggered by Chiral Isotopomer Arising from Oxygen Isotope Substitution
Author(s) -
Kawasaki Tsuneomi,
Okano Yasushi,
Suzuki Etsuharu,
Takano Shizuka,
Oji Shotaro,
Soai Kenso
Publication year - 2011
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.201102263
Subject(s) - autocatalysis , isotopomers , enantioselective synthesis , chemistry , oxygen , chirality (physics) , isotopes of oxygen , substitution (logic) , kinetic isotope effect , stereochemistry , catalysis , organic chemistry , physics , chiral anomaly , nuclear chemistry , molecule , deuterium , computer science , particle physics , quantum mechanics , nambu–jona lasinio model , programming language , fermion
Trigger happy : Chiral oxygen isotopomers of hydrobenzoin ([ 18 O]( R )‐ 1 and [ 18 O]( S )‐ 1 ) acted as chiral triggers to induce the enantioselective addition of i Pr 2 Zn to pyrimidine‐5‐carbaldehyde. An extremely small chiral influence arising from the presence of the oxygen isotope ( 18 O) is amplified through asymmetric autocatalysis to enantioenrich the 5‐pyrimidyl alkanol product.