Unknown

Dataset Information

0

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


ABSTRACT: 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.

SUBMITTER: Bajtel A 

PROVIDER: S-EPMC8111431 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC4599979 | biostudies-literature
| S-EPMC5129522 | biostudies-literature
| S-EPMC395981 | biostudies-literature
| S-EPMC3014220 | biostudies-literature
| S-EPMC10745768 | biostudies-literature
| S-EPMC9686613 | biostudies-literature
| S-EPMC4959890 | biostudies-literature
| S-EPMC3163040 | biostudies-literature
| S-EPMC7431042 | biostudies-literature
| S-EPMC9192141 | biostudies-literature