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Asymmetric Amplification Using Chiral Cocrystals Formed from Achiral Organic Molecules by Asymmetric Autocatalysis
Author(s) -
Kawasaki Tsuneomi,
Jo Kazumichi,
Igarashi Hirotaka,
Sato Itaru,
Nagano Masaki,
Koshima Hideko,
Soai Kenso
Publication year - 2005
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.200462963
Subject(s) - autocatalysis , enantioselective synthesis , chemistry , phenanthridine , enantiomer , homochirality , chirality (physics) , molecule , enantiomeric excess , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , chiral symmetry breaking , nambu–jona lasinio model , physics , quantum mechanics , quark
Enantioselective addition of diisopropylzinc to a pyrimidine‐5‐carbaldehyde was induced by chiral cocrystals of achiral two‐component molecular crystals of tryptamine/ para ‐chlorobenzoic acid (see scheme) and 3‐indolepropionic acid/phenanthridine. This reaction, in conjunction with asymmetric autocatalysis, afforded a pyrimidyl alkanol in high enantiomeric excess.