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 (−)-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 reg…
CCDC 2063843: Experimental Crystal Structure Determination
Related Article: Ákos Bajtel, Mounir Raji, Matti Haukka, Ferenc Fülöp, Zsolt Szakonyi|2021|Beilstein J.Org.Chem.|17|983|doi:10.3762/bjoc.17.80
CCDC 2063842: Experimental Crystal Structure Determination
Related Article: Ákos Bajtel, Mounir Raji, Matti Haukka, Ferenc Fülöp, Zsolt Szakonyi|2021|Beilstein J.Org.Chem.|17|983|doi:10.3762/bjoc.17.80