DIRECTIVE EFFECTS IN THE OPENING OF EPOXIDES WITH TRIMETHYLSILYL CYANIDE- ZINC IODIDE. THE ESTABLISHMENT OF THREE CONTIGUOUS CHIRAL CENTERS.

Article abstract of DOI:10.1016/S0040-4039(01)81357-5

Adjacent hydroxyl, trimethylsiloxyl, and acetoxyl groups have been shown to provide complete control over the regiospecifity of the opening of epoxides by trimethylsilyl cyanide - zinc iodide.Thus, cyclohex-2-en-R-1-ol can be readily converted into (1R,2S,3R)-3-aminocyclohexan-1,2-diol.