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

The KabachnikFields reaction of E,Z-citral with diethyl phosphite in the presence of isobutylamine has been found to form a-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 a-aminophosphonates. We have managed to synthesize a-aminophosphonates by the reaction of O,O-dialkyl trimethylsilyl phosphites with prenyl imines in the presence of water or diethylamine. a-Aminophosphonates were also synthesized by the reaction of diethyl phosphite with (R,S)-citronellal in the presence of alkylamines. a-Aminophosphonates obtained showed bacteriostatic activity against Staphylococcus aureus and Bacillus cereus. (c) 2012 Wiley Periodicals, Inc. Heteroatom Chem 24:3642, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21060