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Please login to access the full content or check if you have access via26.9.1.1.3.13 Variation 13: Addition of Organometallics to α,β-Unsaturated Nitriles
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Marsden, S. P., Science of Synthesis, (2005) 26, 1063.
Unsaturated nitriles undergo nucleophilic attack at the cyano group by both Grignard reagents[76] and organolithiums,[77] leading, upon hydrolytic workup, to the corresponding enones. The conversion of nitrile 84 into cis-α-irone (85, Scheme 20) is particularly noteworthy since complications may also have arisen from competing deprotonation at the doubly activated γ-position.
Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeee ee ee α,β-Meeeeeeeeee Meeeeee[88]
Meeeeeeeeeee Meeeeeeee
eee-α-Meeee (88); Meeeeee Meeeeeeee:[88]
M 8.8 M eeee ee MeMe ee Me8M (8.88 eM) eee eeeee ee e eeeeeee eeee ee eeeeeee 88 (88 ee, 8.88 eeee) ee Me8M (8.8 eM) ee −88°M. Mee eeeeeee eee eeeeeeeee eeeeee ee −88°M eeee 8 e eee eeee eeeeeeeeee ee −8°M eee 88 eee. Mee eeeeeeee eee eeeeeeee eeee e eee. ee MM8Me eeee ee 8°M. Meeee eeeeeeee eee 88 eee, eee eeeeeee eee eeeeeee eeee Me8M, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) ee eeee e eeeee eeeeee (88%) ee eeeee-α-eeeee eeeeeeee ee eee-α-eeeee (88); eeeee: 88 ee (88%).
References
| [76] | Meeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [77] | Meeeeee, M.; Meee, M.; Meeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
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