Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols
Bajtel, Á., Raji, M., Haukka, M., Fülöp, F., & Szakonyi, Z. (2021). Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols. Beilstein Journal of Organic Chemistry, 17, 983-990. https://doi.org/10.3762/bjoc.17.80
Published inBeilstein Journal of Organic Chemistry
© 2021 the Authors
A library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (−)-α-pinene was converted into condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray spectroscopic techniques. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from the commercially available (1R)-(−)-myrtenol (10). The reduction or alkaline hydrolysis of the oxazolidines, followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.