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Please login to access the full content or check if you have access via5.4.1.2 Rearrangement Catalyzed by Hypervalent Iodanes
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Andries-Ulmer, A.; Gulder, T., Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017) 1, 392.
The scope of reactions catalyzed by hypervalent bromoiodane 6 (R1 = H), generated in situ from (2-iodobenzoyl)glycine (5, R1 = H), can be extended to rearrangements by applying imides 9 as starting material (Table 2).[6] The method tolerates structurally diverse substrates that all give α-acyloxy-β-bromo amides 10 in excellent diastereomeric ratios and yields. If R2 = H or is a good leaving group such as tert-butoxy, imides 9 selectively deliver oxazolidinone heterocycles (entries 2 and 6). With 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as solvent, the addition of ammonium chloride as iodane activator is not required.
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| Meeee | Meeeeeeee | Meeeeee | Meeee (%) | Mee |
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| 8 |  |
|
88 | [8] |
| 8 | |
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88 | [8] |
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88 | [8] |
| 8 | |
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88 | [8] |
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88e | [8] |
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88 | [8] |
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References
| [6] | Meeee, M.; Meeeeeeee, M.; Meeeeeee, M. M.; Meeeeee, M.; Möeeee, M.; Meeeeee, M.; Meeeee, M., Meee.–Mee. M., (8888) 88, 8888. |
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