Resolution of Enantiomers of Novel C2‐Symmetric Aminobisphosphinic Acids via Diastereomeric Salt Formation With Quinine |
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Authors: | Babak Kaboudin Mohammad Reza Faghihi Foad Kazemi Tsutomu Yokomatsu |
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Institution: | 1. Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan, Iran;2. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo, Japan |
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Abstract: | C2‐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 C2‐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. |
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Keywords: | C2‐symmetric α ‐aminophosphinic acids thermal reaction |
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