Asymmetric amino-hydroxylation of dienylsilanes. An efficient route to amino-cyclitols

Article abstract of DOI:10.1016/S0040-4039(97)00079-8

Sharpless asymmetric amino-hydroxylation of a silyl-2,5-cyclohexadiene occurs with complete regio- and diastereocontrol. An enantioselectivity of up to 68% e.e. was also observed. An application of the methodology to the synthesis of relevant examples of amino-cyclitols is described.