2000 oxazole derivatives

oxazole derivativesR 0220

20 - 106N-Carbamoylamino Alcohols as the Precursors of Oxazolidinones viaNitrosation-Deamination Reaction. — Treatment of N-carbamoylaminoalcohols (I) with NO+ [cf. conditions A)] effectively yields oxazolidines of type(II). Addition of an organic cosolvent sometimes improves slightly the yield.Dynamic kinetic resolution of the DL-phenylalanine derivative (V) allows anaccess to the chiral N-carbamoylamino alcohol (VII) as precursor of (R)-4-benzyloxazolidinone (IIa). The latter is converted to Wittig phosphorane (XII),a suitable synthon in natural product preparation. — (SUZUKI, MASAMI;YAMAZAKI, TAKAHIRO; OHTA, HIROMICHI; SHIMA, KYOKO; OHI,KATSUHIDE; NISHIYAMA, SHIGERU; SUGAI, TAKESHI; Synlett (2000) 2,189-192; Dep. Chem., Fac. Sci. Technol., Keio Univ., Kohoku, Yokohama 223,Japan; EN)

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