Intramolecular Aminoalkoxylation of Unfunctionalized Olefins via Intramolecular Iodoamination and Aziridinium Ion Ring-Opening Sequence

The
preparation of prolinol ether type compounds was realized via
MnI2-catalyzed intramolecular iodoamination of unfunctionalized
olefins and subsequent ring opening of an aziridinium ion intermediate
with alcohols/phenols. In the presence of a catalytic amount of MnI2 and 2 equiv of NaI, intramolecular aminoalkoxylation of different N-benzyl-5-methylhex-4-en-1-amine substrates proceeded readily
in alcoholic solvents, leading to 2-(alkoxyalkyl)­pyrrolidine products
in up to 90% isolated yields.