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Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
Author(s) -
Matsumoto Arimasa,
Abe Takaaki,
Hara Atsushi,
Tobita Takayuki,
Sasagawa Taisuke,
Kawasaki Tsuneomi,
Soai Kenso
Publication year - 2015
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.201508036
Subject(s) - autocatalysis , tetramer , homochirality , alkoxide , chemistry , crystallization , oligomer , enantiomeric excess , enantiomer , crystallography , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , enzyme
Asymmetric amplification during self‐replication is a key feature that is used to explain the origin of homochirality. Asymmetric autocatalysis of pyrimidyl alkanol in the asymmetric addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde is a unique example of this phenomenon. Crystallization of zinc alkoxides of this 5‐pyrimidyl alkanol and single‐crystal X‐ray diffraction analysis of the alkoxide crystals reveal the existence of tetramer or higher oligomer structures in this asymmetric autocatalytic system.