Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

A library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (?)-?-pinene converted into condensed oxazolidin-2-one two steps by carbamate formation followed aminohydroxylation process. The relative stereochemistry the pinane-fused determined 2D NMR and X-ray spectroscopic techniques. regioisomeric spiro-oxazolidin-2-one similar way starting commercially available (1 R )-(?)-myrtenol ( 10 ). reduction or alkaline hydrolysis oxazolidines, reductive alkylation resulted primary secondary 2-amino-1,3-diols, which underwent regioselective ring closure with formaldehyde benzaldehyde delivering pinane-condensed oxazolidines. During preparation 2-phenyliminooxazolidine, an interesting ring–ring tautomerism observed CDCl 3 .