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Unraveling the Mechanism of the Soai Asymmetric Autocatalytic Reaction by First‐Principles Calculations: Induction and Amplification of Chirality by Self‐Assembly of Hexamolecular Complexes
Author(s) -
Schiaffino Luca,
Ercolani Gianfranco
Publication year - 2008
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.200802450
Subject(s) - autocatalysis , chirality (physics) , mechanism (biology) , asymmetric induction , substituent , reaction mechanism , chemistry , computational chemistry , stereochemistry , organic chemistry , chiral symmetry breaking , catalysis , enantioselective synthesis , physics , symmetry breaking , quantum mechanics , nambu–jona lasinio model
Soai, so good : The Soai reaction is the sole reported case of amplifying asymmetric autocatalysis. A mechanism is proposed for this reaction, supported by first‐principle calculations, clarifying not only the reasons for the detected chiral induction and amplification, but also the roles performed by isopropyl groups, γ‐pyridinic nitrogen atoms, and the δ‐substituent.