lndoline (I) and 2-methylindoline (2) have been converted into indole (3) and 2-methylindole (4), and dibenzylamine ( 7 ) and phenylbenzylamine (8) have been converted into the Schiff bases (9) and (lo), by Swern oxidation; the methylthiomethyl amines (5), ( 6), ( l l ) , and (12) were the only other products formed.
Optically pure (R)and (S)-P-lysines have been obtained via cycloaddition of chiral nitrone (4) to vinyl acetate, followed by facile chromatographic separation of the four resulting acetates (5) into two pairs of C-5 epimers and conversion of each pair into diastereoisomerically pure isoxazolidinone (7a or b).
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