The Kabachnik–Fields and Pudovik Reactions on the Basis of E,Z‐Citral and Its Imines and (R,S)‐Citronellal

The Kabachnik–Fields reaction of E,Z-citral with diethyl phosphite in the presence of isobutylamine has been found to form α-aminophosphonates. The Pudovik reactions of diethyl phosphite with prenyl imines prepared on the basis of E,Z-citral with isobutylamine also allowed us to obtain the same α-aminophosphonates. We have managed to synthesize α-aminophosphonates by the reaction of O,O-dialkyl trimethylsilyl phosphites with prenyl imines in the presence of water or diethylamine. α-Aminophosphonates were also synthesized by the reaction of diethyl phosphite with (R,S)-citronellal in the presence of alkylamines. α-Aminophosphonates obtained showed bacteriostatic activity against Staphylococcus aureus and Bacillus cereus. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 24:36–42, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21060

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