Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids

Article abstract of DOI:10.1016/0040-4039(96)00122-0

New cyclic chiral nitrones constituting two diastereomers were synthesized by the reaction of isonitroso Meldrum's acid with l-menthone via a nitrosoketene intermediate. Both nitrones reacted with allyltrimelhylsilane diastereoselectively to give the corresponding isoxazolidine derivatives as sole products, which were converted to (S)- and (R)-allylglycines in ca. 100% ee, respectively.