ADDITIONS OF 1-(ALPHA-AMINOALKYL)BENZOTRIAZOLES TO ENOL ETHERS - NEW ROUTES TO 1,3-AMINO ETHERS

1-(alpha-Aminoalkyl)benzotriazoles add readily to enol ethers to give the corresponding 1-benzotriazolyl-3-aminoalkyl ethers in high yields. Subsequent replacement of the benzotriazole moiety by an alkyl or aryl group (with a Grignard reagent) or by a hydrogen atom (with lithium aluminum hydride) affords 1,3-amino-ethers in good yields. Anchimeric assistance by the amino groups in the substitutions of the benzotriazolyl moiety facilitates the reactions. Full stereochemistry is assigned to the stereoisomeric products on the basis of NMR techniques and X-ray diffraction.