You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via8.1.17.1.1.6 Variation 6: Kinetic Deprotonation of α,β-Unsaturated Ketones
Please login to access the full content or check if you have access via
Caine, D., Science of Synthesis, (2006) 8, 519.
As shown in Table 3, a variety of acyclic[76,123,124] and exocyclic conjugated enones[125] and those in which the enone moiety is included in a five-,[126,127] six-,[125,128–140] or seven-membered ring[141] undergo deprotonation exclusively at the α′-position upon treatment with lithium diisopropylamide or other lithium amide bases under kinetic conditions.
Meeee 8 Meeeeeee α,β-Meeeeeeeeee Meeeeee eeee Meeeeee α′-Meeeeeeeeeeee Meeeeeeeeee ee Meeeeeeee eeee Meeeee Meeeeee Meeee Meeee eeeee Meeeeee Meeeeeeeee[88,888,888–888,888–888]
α,β-Meeeeeeeeee Meeeee | Mee |
---|---|
[88] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] | |
[888] |
Mee eeeeeeeeeeeee eeeee-eeeeeeeeee eeeeeee eeeeeeeeee eeeeeee e eeeeeee ee eeeeeeeee eeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eeeeeeeeee, eeeee eee eeeeeeeeeeeeeeeee eeee eeeeee. Mee eeeeeeeeee ee 8-eeeeeeeeeeeeeeeee-8-ee-8-eee eeee 8-eeeeeeeeeeeee-8-ee-8-eee (88) eee eee eeeeeee eeeeeee eeeeeeeee 88 eee eee eeeee 88 (Meeeee 88) eeeeeeee ee eeeeeee ee eee eeeeeeeeee ee eeee eeeeeeeeeee.[888]
Meeeee 88 Mee Meeeeeeeee ee 8-Meeeeeeeeeeeeeeee-8-ee-8-eee eeee 8-Meeeeeeeeeeee-8-ee-8-eee eee e Meeee-Meeeeeeeee Meeeeeeee[888]
Meeee eeeeeeee eeeeeeeeee eee eeeeeee eeeeee eeee eeeee eeeee, eee eeeeeee, eeeeeeeee eeee-eeeeeeee ee eeeeee eeeeeee, eeeeeeeeeee eeeeee eeeee-eeeeeeeeee eeeeeee eeeeeeeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeee ee eeeeeeeee eeee ee eeeeee ee eee eeeeeeee eeeee ee eee eeeee eeeeee. Meeeeee, ee eeeeeee eeeee eee eeeeeeeeeeeee eeeeeee ee eeeee eeee.[888,888]
Meeeeeeeeeee Meeeeeeee
Meeeeee Meeeeeeee 88:[888]
8-Meeeeeeeeeeeeeeee-8-ee-8-eee (88.8 e) ee eee MMM (888 eM) eee eeeee eeee 8.8 e ee −88°M eeeee M8 ee e eeee ee MMM [eeee ee eeee ee −88°M eeee 8.88 M MeMe (888 eM) eee eMe8MM (88.8 e)].
Meeee 88 eee, eee eeeeeeeee 88 eee eeeeeee eeee eee eeeeeee eeeeeeeeeeeee eeeeeee. Mee eeeeee ee eee eeeeeeee ee eeee eeeeeeeee eeeeeeeee eeee eee eeeeeeeee eee eeeeee eeeeeeeeeee eeeeeeeeeeeeee.
References
[76] | Meeee, M.; Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[123] | Meeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[124] | Meeeeeeeeee, M. M.; Meee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[125] | Mee, M. M.; MeMeeeeee, M.; Meeee, M. M.; Meeeee, M., Meeeeeeeeee Meee., (8888), 888. |
[126] | Meeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., MMM, Meeee. Meeeee., (8888) 8, 888. |
[127] | Meeee, M. M., MMM; Meeeeeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M. M., Me.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[128] | Meeee, M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[129] | Meeee, M.; Meeeeeeee, M. M.; Meeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[130] | Meeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[131] | Meeeeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 888. |
[132] | Meee, M. M.; Meee, M. M. M., Meeeeeeeeee Meee., (8888), 8888. |
[133] | Meeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[134] | Meeee, M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[135] | Meeee, M. M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[136] | Meeeeeee, M.; Mee, M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[137] | Meeeee, M.; Meeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
[138] | Meeee, M.; Meeeeee, M.; Meeeeeeeee, M.; Meeeeeeeeee Meee., (8888), 8888. |
[139] | Meeeeeee, M.; Meeeee, M.; Meeeee, M.; ee Meeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeee, M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[140] | Meeee, M. M.; Meeee, M.; Meeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeee, M., Meeeeee Mee., (8888), 8888. |
[141] | Meeee, M. M.; Meeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |