Chiral and Achiral N-Phosphonyl Imine Chemistry and Microwave-Assisted Reactions



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The synthesis and characterization of chiral and achiral N-phosphonyl imines has been achieved. Chiral N-phosphonyl imines have been successfully utilized in the asymmetric addition of diethyl phosphate and cyanide to obtain α-amino phosphonates and α-amino nitriles respectively; excellent yields and diastereomeric ratios have been obtained. Achiral N-phosphonyl imines have been effectively used in the asymmetric addition of cyanide in an enantioselective fashion by using a chiral amino acid, a chiral amino alcohol or chiral BINOL derivatives. All products can be purified by GAP (Group-Assistant-Purification) chemistry. In addition, the use of microwave irradiation for multicomponent domino reactions has been achieved. Quinazolines were obtained from aromatic aldehydes, 2-cyanoacetamide and cyclopentanone. Spirocyclic compounds have also been obtained from isoxazoles, aromatic aldehydes and Meldrum’s acid. The formation of various chiral centers was obtained in a regioselective manner for both reactions.