A novel method for the separation of bis(alpha-hydroxyalkyl)phosphinic acid diastereoisomers via formation of novel cyclic phosphinic acids.
The reaction of aromatic and aliphatic aldehydes with hypophosphorus acid under microwave irradiation was examined. The reaction gave a mixture of a racemic pair of bis(alpha-hydroxyalkyl)phosphinic acids and acetal derivatives from the corresponding bis(alpha-hydroxyalkyl)phosphinic acids of meso-stereochemistry in good yield. The difference in solubility in organic solvents due to polarity allowed us to readily separate these compounds. This method constitutes an easy, rapid, and good-yielding preparation and separation of bis(alpha-hydroxyalkyl) phosphinic acid diastereoisomers from simple starting materials using microwave irradiation.
Kaboudin
Babak
B
Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, Zanjan 45195-1159, Iran. kaboudin@iasbs.ac.ir
Haghighat
Hamideh
H
Yokomatsu
Tsutomu
T
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D010721:Phosphinic Acids; D006859:Hydrogen