2- Amino alcohols from 2-oxazolone

Catalytic hydrogenation of the exocychc double bond of several oxazolones 611, in the presence of acetic acid, gives a-acylamino alcohols 613 via the saturated derivatives 612 (Scheme 7.196). Selected examples of amino acid derivatives and amino alcohols available from reduction of unsaturated oxazolones are shown in Table 7.45 (Fig. 7.56). 

TABLE 7.45. AMINO ACID, AMINO ESTER AND AMINO ALCOHOL DERIVATIVES FROM HYDROGENATION OF UNSATURATED 5(4//)-OXAZOLONES... 

The relative stereochemistry of both 2-amino and 3-hydroxy groups in Leucetta-mols A and B, two antimicrobial lipids, has been defined by analysis of nuclear Overhauser enhancements in bis(oxazolone) 694, which was formed by treatment of 693 with GDI [459]. The absolute stereochemistry of sphingosine-related polyunsaturated 2-amino alcohols isolated from marine organisms as secondary metabolites was also assigned by transformation to the oxazolidin-2-one and examination of the NMR data [460]. 

---