TY - JOUR
T1 - Molecular-level chiral discrimination and induction
AU - Saigo, Kazuhiko
AU - Hashimoto, Yukihiko
AU - Kinbara, Kazushi
AU - Sudo, Atsushi
N1 - Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 1996
Y1 - 1996
N2 - The review describes the mechanism of chiral discrimination of racemic amines upon crystallization and the induction of chirality in organic reactions by using them as chiral auxiliaries. In order to form conglomerates, which can be resolved into the two enantiomers upon alternative seeding, both formation and packing of 21-columns are essentially very important. On the other hand, in order to achieve high efficiency in resolution through diastereomeric salt formation, which is the most practical method, one of a pair of diastereomeric salts derived from a racemic amine and an enantiomerically pure resolving agent should at least have two 2,-columns and planar boundary surfaces in its crystal structure. On the basis of this knowledge, we developed several artificial chiral auxiliaries such as erythro2-amino-l,2-diphenylethanol, cis-2-amino-l-acenaphthenol, and cis-2- amino-3,3dimethyl-1-indanol. These were found to be very efficient chiral auxiliaries in asymmetric inductions: alkylation of chiral imines, catalytic borane-reduction, and alkylation of chiral N-acylated oxazolidinone.
AB - The review describes the mechanism of chiral discrimination of racemic amines upon crystallization and the induction of chirality in organic reactions by using them as chiral auxiliaries. In order to form conglomerates, which can be resolved into the two enantiomers upon alternative seeding, both formation and packing of 21-columns are essentially very important. On the other hand, in order to achieve high efficiency in resolution through diastereomeric salt formation, which is the most practical method, one of a pair of diastereomeric salts derived from a racemic amine and an enantiomerically pure resolving agent should at least have two 2,-columns and planar boundary surfaces in its crystal structure. On the basis of this knowledge, we developed several artificial chiral auxiliaries such as erythro2-amino-l,2-diphenylethanol, cis-2-amino-l-acenaphthenol, and cis-2- amino-3,3dimethyl-1-indanol. These were found to be very efficient chiral auxiliaries in asymmetric inductions: alkylation of chiral imines, catalytic borane-reduction, and alkylation of chiral N-acylated oxazolidinone.
KW - Artificial chiral auxiliaries
KW - Chiral discrimination
KW - Chiral induction
KW - Diastereomeric salts
KW - Racemic amines
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U2 - 10.1007/bf02896330
DO - 10.1007/bf02896330
M3 - Article
AN - SCOPUS:0040879093
VL - 108
SP - 555
EP - 573
JO - Proceedings of the Indian Academy of Sciences - Section A
JF - Proceedings of the Indian Academy of Sciences - Section A
SN - 0974-3626
IS - 6
ER -