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Resolution of Enantiomers of Novel C 2 ‐Symmetric Aminobisphosphinic Acids via Diastereomeric Salt Formation With Quinine
Author(s) -
Kaboudin Babak,
Faghihi Mohammad Reza,
Kazemi Foad,
Yokomatsu Tsutomu
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22391
Subject(s) - diastereomer , chemistry , enantiomer , salt (chemistry) , amine gas treating , crystallization , stereochemistry , brucine , medicinal chemistry , fractional crystallization (geology) , organic chemistry , biochemistry , strychnine , geochemistry , basalt , geology
C 2 ‐symmetric N,N ‐bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C 2 ‐symmetric N,N ‐bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation with (–)‐quinine, and subsequent fractional crystallization. X‐ray crystallographic analysis of one of the diastereomeric salts clearly revealed that (–)‐quinine could be an efficient resolving agent for obtaining the single enantiomer ( R , R)‐N,N ‐bis(phosphinomethyl)amine. Chirality 27:71–74, 2015 . © 2014 Wiley Periodicals, Inc.