You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via11.12.1.5.1.2 Method 2: Cyclization of β-(Acyloxy)-N,N-bis(trimethylsilyl)enamines
Please login to access the full content or check if you have access via
Boyd, G. V., Science of Synthesis, (2002) 11, 442.
β-(Acyloxy)-N,N-bis(trimethylsilyl)enamines 236 are converted into oxazoles 1 (Scheme 103) by the action of trimethylsilyl trifluoromethanesulfonate (Method A) or by flash vacuum pyrolysis (Method B).[170,171]
Meeeee 888 Meeeeeeeeee Meeeeeee eeee eee Meeeeeeeeee ee β-(Meeeeee)-M,M-eee(eeeeeeeeeeeeee)eeeeeeee[888,888]
M8 | M8 | M8 | Meeeeee | Meeee (e) | Meeee (%) | Mee |
---|---|---|---|---|---|---|
Me | Me | Me | M | 8 | 88 | [888] |
Me | Me | Me | M | e.e. | 88 | [888] |
MM=MMMe | Me | Me | M | e.e. | 88 | [888] |
MM8Me | Me | Me | M | e.e. | 88 | [888] |
MM8 | Me | Me | M | e.e. | 88 | [888] |
Me | Me | Me | M | e.e. | 88 | [888] |
M | Me | Me | M | 8 | 88 | [888] |
Me | MM8MM=MM8 | Me | M | 8 | 88 | [888] |
Me | eeeeeeeeeee | Me | M | 8 | 88 | [888] |
Me | Me | Me | M | e.e. | 88 | [888] |
Me | MM=MM8 | Me | M | e.e. | 88 | [888] |
Me | M-eMe8 | eMe | M | e.e. | 88 | [888] |
Me | Me | Me | M | e.e. | 88 | [888] |
MM8 | Me | Me | M | e.e. | 88 | [888] |
e Meeeee M: MMMMMe; Meeeee M: Meeee eeeeee eeeeeeeee. Mee eeeeeeeeeeee eeeeeeeeee eee eeeeeee.
e e.e. = eee eeeeeeee.
Meeeee M ee eeeeeeeeee eee eeeeeeeee ee eeee eeeeeeeee eeeeee; eeeeeeee, ee Meeeee M eee eeeeeeee eeee ee ee eeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeee.
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee Meeeeeee 8; Meeeeee Meeeeeeeee:[888,888]
Meeeee M: M eeee ee eee β-(eeeeeee)eeeeeee 888 (8.8–8.8 eeee) eee MMMMMe (8.8–8.8 eeee) ee MMMe8 ee MM8Me8 (8–8 eM) eeeee eeeee ee e eeeee eeeeee eeee Meeeeeee eee eeeeeee ee ee eee eee eeeeeeeee eeee (Meeeee 888). Mee eeeeeee eee eeeeee ee ee eeeeeeeeeeeeee ee eeeee eeeeeee, ee ee eeeeeeee ee eeeeeee eee ee MeMMM8, eeeeeeeeee ee eee eeeeeee eeeee, eee eeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeee eeee. Mee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee ee Me8M/eeeeee 8:88).
Meeeee M: Mee β-(eeeeeee)eeeeeee 888 (8.8–8.8 eeee) eee eeeeeeeeeee (ee eeeeeee ee ee eee eeee ee eeeeeeeee) eeee e 88.8 ee × 8.88 ee eeeeee Meeeeee eeee eeee ee 888°M/8 Meee. Mee eeeeeeeeee eee eeeeeeeee ee −88°M eee eee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee.
References
[170] | Meeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[171] | Meeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.