Alkyl ethers of alpha-amino oxime of the pinane series as a platform for the synthesis of highly lipophilic alpha-aminophosphonates
T. C. WANG, A. M. AGAFONTSEV, A. A. NEFEDOV, A. V. TKACHEV
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: terpenes, oxime ethers, aminophosphonates, Kabachnik-Fields reaction, stereoselectivity
Abstract
A method to synthesis new hybrid derivatives of α-pinene with α-aminophosphonate fragment has been developed to obtain an additional centre of metal coordination in the molecules of potential extractants for heavy metals. It has been shown that O-alkyl ethers of α-amino oximes of the pinane series can be converted according to the two-stage version of Kabachnik-Fields reaction with dimethylphosphite and benzaldehyde into new chiral α-aminophosphonates with a satisfactory preparative yield (40-42 %). According to this scheme, terpene aminophosphonates are obtained as highly lipophilic products in the form of a pair of stereoisomers with a diastereomeric purity of 49-66 %.
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