1292323-11-5Relevant articles and documents
(2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates
El-Gokha, Ahmed,Maas, Gerhard
, p. 2849 - 2857 (2011)
A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1- phenylcyclopropyl)phosphonate ((Z)-6, (E)-6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the Z/E ratio of 6. By reaction with benzylamine or methyl esters of glycine, (S)-alanine, and (S)-phenylalanine, the Z/E-mixture of 6 was converted into cyclopropylaldimines, which after reduction gave the corresponding N-substituted (2-aminomethyl-cyclopropyl)phosphonates.