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20.2.7.1.2.3.2.1 Variation 1: Intramolecular Nucleophilic Nitrogen Addition to Epoxides To Generate ­Cyclic Carbamates

DOI: 10.1055/sos-SD-020-00343

Wolkenberg, S. E.; Garbaccio, R. M.Science of Synthesis, (200720397.

Oxazolidinone 32 is available from 2,3-epoxy alcohol 31 by cyclization using sodium hydride in the presence of methyl isocyanate; the epoxide opening proceeds with clean inversion to give a 3:2 regioisomeric mixture of carbamates (Scheme 11). The 4-alkenyloxazolidinone 32 can be equilibrated to a 1:1 mixture of 4- and 5-alkenyloxazolidinones; in this way, material can be cycled to the primary alcohol 33, which is oxidized under standard conditions to 34.[‌59‌] Hydrolysis of the carbamate provides the β-hydroxy-α-amino acid 35.[‌60‌]

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