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Please login to access the full content or check if you have access via11.12.1.5.1.1 Method 1: Intramolecular Aza-Wittig Reaction of β-(Acyloxy)vinyl Azides
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Boyd, G. V., Science of Synthesis, (2002) 11, 441.
The base-induced acylation of α-azido ketones 222 with acid chlorides or anhydrides gives the Z-enol esters 234 stereoselectively. Treatment of the latter with triethyl phosphite produces oxazoles 1 via the unisolable intermediates 235 (Scheme 102).[169]
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| M8 | M8 | M8 | Meeeee (%) | Mee |
|---|---|---|---|---|
| Me | M | Me | 88 | [888] |
| Me | M | 8-MeM8M8 | 88 | [888] |
| Me | M | 8-eeeee | 88 | [888] |
| Me | Me | Me | 88 | [888] |
| Me | eMe | Me | 88e | [888] |
| eeeeeeeeeee | M | Me | 88 | [888] |
| Me | M | Me | 88 | [888] |
| 8-eeeeeee | M | Me | 88 | [888] |
| 8-eeeee | M | 8-eeeee | 88 | [888] |
e Meee eeeee 888.
e Mee eeeeeeee eee eeeeeee eee ee ee.
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee Meeeeeee 8; Meeeeee Meeeeeeee:[888]
(MeM)8M (8.88 e, 88 eeee) eee eeeee ee e eeeeeee eeee ee e β-(eeeeeee)eeeee eeeee 888 (8.88 eeee) ee eeeeeeeeeee (8 eM). Meeeeeeee ee M8 eeeee ee eeee eee eeeeee eeeee 8 e. Mee eeee eee eeeeee ee e eeeeee eeee eee eeeeeee eeeeeeeeeeee ee 88°M eee 88 e. Mee eeeeeee eee eeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8).
References
| [169] | Meeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) M 8e, 888.
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