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Self‐Replication and Amplification of Enantiomeric Excess of Chiral Multifunctionalized Large Molecules by Asymmetric Autocatalysis
Author(s) -
Kawasaki Tsuneomi,
Nakaoda Mai,
Takahashi Yutaro,
Kanto Yusuke,
Kuruhara Nanako,
Hosoi Kenji,
Sato Itaru,
Matsumoto Arimasa,
Soai Kenso
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405441
Subject(s) - autocatalysis , stereocenter , chirality (physics) , chemistry , molecule , diastereomer , asymmetric carbon , enantiomer , homochirality , enantiomeric excess , enantioselective synthesis , combinatorial chemistry , reagent , stereochemistry , nanotechnology , organic chemistry , materials science , catalysis , chiral symmetry breaking , optically active , symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model
Self‐replication of large chiral molecular architectures is one of the great challenges and interests in synthetic, systems, and prebiotic chemistry. Described herein is a new chemical system in which large chiral multifunctionalized molecules possess asymmetric autocatalytic self‐replicating and self‐improving abilities, that is, improvement of their enantioenrichment in addition to the diastereomeric ratio. The large chiral multifunctionalized molecules catalyze the production of themselves with the same structure, including the chirality of newly formed asymmetric carbon atoms, in the reaction of the corresponding achiral aldehydes and reagent. The chirality of the large multifunctionalized molecules controlled the enantioselectivity of the reaction in a highly selective manner to construct multiple asymmetric stereogenic centers in a single reaction.