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Asymmetric Autocatalysis Triggered by Chiral Crystals Formed from Achiral Compounds and Chiral Isotopomers
Author(s) -
Kawasaki Tsuneomi,
Soai Kenso
Publication year - 2012
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201100155
Subject(s) - autocatalysis , homochirality , chemistry , enantioselective synthesis , enantiomeric excess , chirality (physics) , asymmetric carbon , enantiomer , stereochemistry , organic chemistry , computational chemistry , catalysis , chiral anomaly , physics , optically active , nambu–jona lasinio model , fermion , quantum mechanics
Asymmetric autocatalysis with amplification of enantiomeric excess is found in the enantioselective addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde using pyrimidyl alkanol as an asymmetric autocatalyst. Asymmetric autocatalysis has been employed as a method for clarifying the origin of homochirality. Circularly polarized light, inorganic chiral crystals and statistical fluctuation of enantiomeric imbalance act as chiral initiators in asymmetric autocatalysis to afford highly enantioenriched products. We have investigated asymmetric autocatalysis using chiral crystals formed from achiral and racemic compounds as an origin of chirality. Absolute control of the crystal chirality of cytosine was achieved by the removal of crystal water. Enantioselective carbon‐carbon bond formation at the enantiotopic crystal face of aldehydes was established using diisopropylzinc vapor. In addition, asymmetric autocatalysis triggered by chiral compounds arising from H, C and O isotope substitution has been achieved.