Resolution of Enantiomers of Novel C2‐Symmetric Aminobisphosphinic Acids via Diastereomeric Salt Formation With Quinine. Issue 1 (16th October 2014)

• Record Type: Journal Article
• Authors: Kaboudin, Babak; Faghihi, Mohammad Reza; Kazemi, Foad; Yokomatsu, Tsutomu
• Is Part Of: Chirality. Volume 27:Issue 1(2015)
• Page Start: 71
• Page End: 74
• Publication Date: 2014-10-16
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22391
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p> <italic>C</italic> ₂‐symmetric <italic>N, N</italic>‐bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of <italic>C</italic>₂‐symmetric <italic>N, N</italic>‐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 (<italic>R</italic>, <italic>R)‐N, N</italic>‐bis(phosphinomethyl)amine. <italic>Chirality 27:71–74, 2015</italic>. © 2014 Wiley Periodicals, Inc.</p> </abstract>