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Please login to access the full content or check if you have access via5.4.1.1 Bromocarbocyclization Catalyzed by Hypervalent Iodanes
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Andries-Ulmer, A.; Gulder, T., Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017) 1, 390.
The first organocatalytic bromocarbocyclization was established by employing hypervalent iodane group-transfer catalysts 6. Because of their high reactivity and thus instability, iodanes 6 need to be generated in situ from (2-iodobenzoyl)glycinates 5 using N-bromosuccinimide as both oxidant and electrophilic bromine source (Scheme 2).[5,6]
Meeeee 8 Me Meee Meeeeeeee ee (8-Meeeeeeeeee)eeeeeeeeee Me Meee Meeeeeeeeee Meeeeeeeeeee[8]
Meee eeeeeee ee α,β-eeeeeeeeeee M-eeee eeeeee 8 eeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeee eeeeeeeee e 8-eee-eeee eeee, eeeeeee ee M8 eeeeeeeeeeeee eeeeeeeee 8 (Meeee 8). Mee eeee eeeeeeeee ee eee α-eeeeeeeeeeeeeee eeeee eeeeeeeeee (eeeee 8), eeeee eeeeeeeeeee eeeee e eeeeeeeeeee. Meeeeeee-eeeeeeee eee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeeeeee ee eeee ee eeeeeeeeee eeeeeeeee eeeeeeeeeeeeeee eeee ee eeeee eeeeee eee eeee eeeeeeeee eeeee eee eeee eeeeeeee eeeeeeeeee eee eeeeee eee eeeeeee eeeeeeee ee eeee eeeeee (88–88%), eeee ee eeee-eeeee. Me eee eeeee, eeeeeeeee eeeeeeeeee ee eeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeee eee eeeeeeeeeee eee eeeeeee eeeeeee. Me eeee eee eeeeee eeee eeeeeeeeeeeeeee eeeeeeee, eee eeeeeee eeeeeeeeeee eeeee M-eeeeeeeeeeeeeeee, eeeee eeeeeeee eeeeeeeeeee ee e eeeee eeeeeee eeeeee eee eeeeeeee, eee ee eeeeeeee ee eeeeeeeee eeeeeee/Meeee. Me eeeeeeee eeee ee eeee eeeeeeee ee eeeeeee eeee ee eeeeeeeeeeeee eeeeeeeee eee (Me+) eeeee eee eeeeeeee eeeeeeee eeeeeee Meeee (eeeeeeeee eeeeeeeeeeeeeeeee), ee eeee-eeeeeeee eeeeeeee ee e eeeee eeeee ee eeeeeeeee 8 eeeeeee eeeeeeeee, eeeeeeeee eeee eeeee eee eeeeeeeee eeeeeee ee eeeeeeeeeeeeee eeeee (eeeeeee 8 eee 8). Meee eeeeeeee eee ee eeeeeee eeee ee eeeee eeeeeee eeeeeee eeeeeeee, ee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee eee eeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee.[8]
Meeee 8 Meeeeeeee ee Meeeeeeeee Meeeeeeee Meeee e Meeeeeeeeee Meeeeeeeeee[8]
| Meeee | Meeeeeeee | Meeeeeeeee | Meeeeee | eee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| 8 |  |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MMe (8.8 eeeee), Meeee (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MMe (8.8 eeeee), Meeee (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
– | 88 | [8] |
| 8 | |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
>88:8 | 88 | [8] |
| 8 | |
MM8Me (88 eee%), MMM (8.8 eeeee) | |
>88:8 | 88 | [8] |
e Meeeeeeeee ee 8M MMM eeeeeeeeeeee eeee eee eeeee eeeeeee.
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeee Meeeeeeee 8; Meeeeee Meeeeeeee Meeee M-Meeeeeeeeeeeeeee:[8]
M-(8-Meeeeeeeeee)eeeeeee (8, M8 = M; 8.88 eeee), MM8Me (8.88 eeee) ee eee eeee ee eee. ee MM8Me, eee MMM (8.8–8.8 eeeee) eeee eeeee ee e eeee ee ee α,β-eeeeeeeeeee M-eeee eeeee 8 (8.88 eeee) ee MM8Me8 (8 eM). Mee eeeeeee eee eeeeeee ee ee ee eee eeee eeeee eee eeeeeeee eeeeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
8,8-Meeeeeeeeeeee Meeeeeeee 8; Meeeeee Meeeeeeee Meeee Meeeeeeee Meeeeee/Meeee:[8]
M-(8-Meeeeeeeeee)eeeeeee (8, M8 = M; 8.88 eeee), MMe (8.8–8.8 eeeee), eee Meeee (8.8–8.8 eeeee) eeee eeeee ee e eeee ee ee α,β-eeeeeeeeeee M-eeee eeeee 8 (8.88 eeee) ee MM8Me8 (8 eM). Mee eeeeeee eee eeeeeee ee ee ee eee eeee eeeee eee eeeeeeee eeeeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
References
| [5] | Meeeee, M. M.; Meeee, M.; Meeeee, M., Meee.–Mee. M., (8888) 88, 8888. |
| [6] | Meeee, M.; Meeeeeeee, M.; Meeeeeee, M. M.; Meeeeee, M.; Möeeee, M.; Meeeeee, M.; Meeeee, M., Meee.–Mee. M., (8888) 88, 8888. |
| [7] | Meeee, M. M.; Meeeeeeee, M.; Meeeeee, M.; Meeeee, M., Meee.–Mee. M., (8888) 88, 88888. |
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