Synthesis of alpha-aminophosphonates from O-methyl esters of monoterpene alpha-aminooximes and aromatic aldehydes
K. S. MARENIN, 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, Pudovik reaction, stereoselectivity
Abstract
It has been shown that O-methyl esters of α-aminooximes of the pinane and karan series can be converted into new chiral α-aminophosphonates by the Kabachnik-Fields and Pudovik reactions with dimethylphosphite and a number of aromatic aldehydes, with preparative yields of up to 80 %. The products are formed as a pair of diastereomers, the ratio of which depends on the synthesis conditions.
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