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Asymmetric Strecker Reaction Arising from the Molecular Orientation of an Achiral Imine at the Single‐Crystal Face: Enantioenriched l ‐ and d ‐Amino Acids
Author(s) -
Miyagawa Shinobu,
Yoshimura Koji,
Yamazaki Yusuke,
Takamatsu Naoya,
Kuraishi Tetsuya,
Aiba Shohei,
Tokunaga Yuji,
Kawasaki Tsuneomi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611128
Subject(s) - strecker amino acid synthesis , enantiopure drug , imine , enantioselective synthesis , chirality (physics) , chemistry , enantiomer , amino acid , stereochemistry , organic chemistry , catalysis , chiral anomaly , biochemistry , physics , fermion , quantum mechanics , nambu–jona lasinio model
Abstract Strecker synthesis has long been considered one of the prebiotic reactions for the synthesis of α‐amino acids. However, the correlation between the origin of chirality and highly enantioenriched α‐amino acids through this method remains a puzzle. In the reaction, it may be conceivable that the handedness of amino acids has been determined at the formation stage of the chiral intermediate α‐aminonitrile, that is, the enantioselective addition of hydrogen cyanide to an imine. Herein, an enantiotopic crystal surface of an achiral imine acted as an origin of chirality for the enantioselective formation of α‐aminonitriles by the addition of HCN. In conjunction with the amplification of the enantiomeric excess and multiplication of enantioenriched aminonitrile, a large amount of near enantiopure α‐amino acids, with the l ‐ and d ‐handedness corresponding to the molecular orientation of the imine, is reported.