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Please login to access the full content or check if you have access via20.6.1.3.3 Variation 3: δ-Lactones from the Opening of Epoxides with C3 Building Blocks
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Maier, M. E., Science of Synthesis, (2007) 20, 1451.
The use of C3 nucleophiles that carry a carboxy function or an equivalent thereof in the reaction with epoxides can lead to δ-lactones. One useful reagent in this regard is trimethyl 3-(phenylsulfonyl)orthopropanoate (55), which serves as a practical homoenolate reagent (Scheme 47).[121] Deprotonation next to the sulfonyl group at −78°C, followed by addition of an epoxide at −20°C and acidic workup, causes lactonization to the δ-lactones 110.[122] Upon treatment with base the unsaturated lactones 111 are obtained. The yields are good for monosubstituted epoxides.
Meeeee 88 δ-Meeeeeee eeee Meeeeeee eee Meeeeeeee 8-(Meeeeeeeeeeeee)eeeeeeeeeeeeeee[888,888]
δ-Meeeeee | Meeee (%) | Mee |
---|---|---|
88 | [888,888] | |
88 | [888,888] | |
88 | [888,888] | |
88 | [888,888] | |
88 | [888,888] | |
88 | [888,888] |
M eeeee ee eeeeeee eeeeeeee, eeee ee MM-88-M (888),[888,888] eeeeeee e 8,8-eeeeeee-8M-8-eeeeeeeeee-8-eee (8,8-eeeeeeeeeeeeeeeeee) eeeeeeeee eeeee eeeeeeee e δ-eeeeeee ee e eee eeeeeeeeee eeeeeee (Meeeee 88). Meee eeeeeeeeeeeee eeeeeeeeeee eee ee eeeeeeee eeee eeeeeee eeee eeeeeeeeeee eee eeeeeeee eeeeeeeeee eee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeee eeee ee eeeeeee.[88] Meeee eeeee eeeeeeeeeee eee eeeeeeeeee eeee ee eeeeeeeee eeeeee, eeeeeeeeeeeee eeeeeeee e eeeeeeee eeee. Meee eeee-eeeeeeeeeeeeeee eee eeeeeeeeeeeeeee eeeeeeee, eeee eeeeee eee ee eeeeeeee.[888,888] M eeeeeeeeee ee eeeeeee eeeeeeee ee eeeeeeeee.[88]
Meeeee 88 M δ-Meeeeee eeee e Meeeeeeee Meeeeee Meee Meeee eee ee Meeeeee[88,888,888]
References
[91] | Meeeeeeeee, M. M.; Meee, M. M., Meeeeeeee, (8888), 888. |
[92] | Meeeeeee, M., Meee. Mee., (8888) 88, 888. |
[121] | Me Meeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeeeee, M. M.; Meeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[122] | Meeeeeeee, M. M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[123] | Meeeeeeee, M.; Meeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[124] | Meeee, M. M.; Meeeeeee, M.; Meeeeeeee, M., Mee. M. Mee. Meee., (8888), 888. |
[125] | Meeeeeee, M. M.; Meee, M. M. M.; Mee, M., M. Me. Meee. Mee., (8888) 888, 888. |
[126] | Meee, M.-M.; Mee, M., Meeeeeeeeeee, (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.