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The Origins of Homochirality Examined by Using Asymmetric Autocatalysis
Author(s) -
Soai Kenso,
Kawasaki Tsuneomi,
Matsumoto Arimasa
Publication year - 2014
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201300028
Subject(s) - autocatalysis , homochirality , enantioselective synthesis , chemistry , chirality (physics) , enantiomeric excess , sodium chlorate , enantiomer , stereochemistry , organic chemistry , chiral symmetry breaking , catalysis , physics , nambu–jona lasinio model , quantum mechanics , quark
Pyrimidyl alkanol was found to act as an asymmetric autocatalyst in the enantioselective addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde. Asymmetric autocatalysis of 2‐alkynylpyrimidyl alkanol with an extremely low enantiomeric excess (ca. 0.00005% ee) exhibits enormous asymmetric amplification to afford the same compound with >99.5% ee. This asymmetric autocatalysis with amplification of ee has been employed to examine the validity of proposed theories of the origins of homochirality. Circularly polarized light, quartz, sodium chlorate, cinnabar, chiral organic crystals and spontaneous absolute asymmetric synthesis were considered as possible candidates for the origin of chirality; each could act as a chiral source in asymmetric autocatalysis. Asymmetric autocatalysis can discriminate the isotope chirality arising from the small difference between carbon (carbon‐13/carbon‐12) and hydrogen (D/H) isotopes. Cryptochiral compounds were also discriminated by asymmetric autocatalysis.