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Please login to access the full content or check if you have access via20.2.7.1.2.3.2.1 Variation 1: Intramolecular Nucleophilic Nitrogen Addition to Epoxides To Generate Cyclic Carbamates
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Wolkenberg, S. E.; Garbaccio, R. M., Science of Synthesis, (2007) 20, 397.
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]
Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeee Meeeeee ee Meeeeeee Me Meee Meeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
(8M)-8-[(8M,8M,8M)-8-Meeeeee-8-eeeeeeeee-8-eeee]-8-eeeeeeeeeeeeeeee-8-eee (88) eee (8M,8M)-8-(Meeeeeeeeeeee)-8-eeeeee-8-[(8M,8M)-8-eeeeeeeeee-8-eeee]eeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[88]
Me e eeee ee 88 (8.8 e, 8.8 eeee) ee eee MMM eeeee M8 eee eeeee MeM (8.88 e, 88.8 eeee) eeeeeeee ee MeMMM (8.88 eM, 88.8 eeee). Mee eeeeeee eee eeeeeeee eee 8 e, eeeeee ee 8°M, eee eeeeeeeeee eeee eee. ee MM8Me eeee. Meeee eeeeeeeeee eeee MeMMe, ee eee eeeeee eeee eee. ee MeMe, eeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:8). Mee eeeee eeeeeeee eeeeeeee 88; eeeee: 8.8 e (88%); [α]M −88.8 (e 8.88, MMMe8); 8M MMM (MMMe8, δ): 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.8 (e, 8M), 8.88 (ee, 8M), 8.88 (e, 8M), 8.8 (e, 8M), 8.8 (e, 8M), 8.88 (ee, 8M, M = 8, 88.8 Me), 8.8 (e, 8M). Mee eeeeee eeeeeeee eeeeee eeee eee eeeeee eeee MeMMe/eeeeeeeee eeeee (8:8) eee eeee 88; eeeee: 8.8 e (88%); [α]M −88.8 (e 8.88, MMMe8); 8M MMM (MMMe8, δ): 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M), 8.88 (ee, 8M), 8.88 (e, 8M), 8.8 (e, 8M), 8.88 (e, 8M), 8.88 (ee, 8M, M = 8, 88.8 Me), 8.88 (e, 8M).
Mee eee eeeeeee eeeeeeeeeeeee ee 88 eee eeeeeeee (8.8 e, 8.8 eeee) eee 88% MeM (8.888 e, 8 eeee) ee eee MMM (88 eM) eeee eeeeeee ee ee eee 8 e. Meeee eee eeeee eeeeee, eee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:8) ee eeeeee 88; eeeee: 8.88 e; eee 88; eeeee: 8.88 e.
References
[59] | Meee Mee, M. M.; Meeeee Meee, M. M.; Meee, M. M.; Meeeeeeeeee, M. M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[60] | Meeeee, M. M., Meee. Meee. Meee, (8888) 88, 8888. |