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Note
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13b The epimeric products were purfied by preparative HPLC (acetone:hexane gradient from 1:10 to 20:1 ratios). Compounds 13, 14 and 15 were synthesized from 1 and acetyl hydroxamic acid and N-hydroxyurea. Substituted N-hydroxycarbamates and N-hydroxyureas were prepared by reaction of the corresponding chloroformates in a stirred biphasic water-dichloromethane solution in the presence of 2.0 equiv of hydroxylamine-HCl and 3.0 equiv sodium bicarbonate 12 h; the aqueous layer was acidified with phosphoric acid and the organic layer was concentrated to yield the N-hydroxycarbamate. Compounds 23 and 25, were prepared by reaction of N-carbonylphenoxy-hydroxylamine with piperidine and morpholine, respectively. Compound 24 was formed as a side product when water was present in the Lewis-acid catalyzed reaction mixture. All compounds were characterized by NMR and HRMS.
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