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Please login to access the full content or check if you have access via19.5.14.1.8 Variation 8: Reaction with Alkenes and Alkynes Bearing Electron-Withdrawing Groups (Michael Addition)
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Murahashi, S.-I., Science of Synthesis, (2004) 19, 354.
Using dihydridotetrakis(triphenylphosphine)ruthenium(II) as a catalyst, the Michael reaction of nitriles is also performed highly efficiently under neutral reaction conditions (Scheme 14). Thus, the addition of nitriles to α,β-unsaturated aldehydes proceeds chemoselectively.[42,43]
Meeeee 88 Meeeeeeeeeeeee Meeeeee Meeeeeeee ee Meeee 8-Meeeeeeeeeeeeee[88,88]
Meeeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M) ee eeee e eeee eeeeeeee eee eee Meeeeee eeeeeeee ee eeeeeeee,[88] eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeee eee eee eeeeeeeeeeee eeee eeeeeeee eeeeeeeee.
Mee eeeeeeeee eee ee eeeeeee ee eee eeeeeeee ee eeeeeeee ee eeeeee (Meeeee 88). Mee eeeeeeee ee 8-eeeeeeeeeeeeeeeeeee eeee eeeeee 8-[(8-eeeeeeeeeeeeeeeee)eeeee]eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) (e.e., ee eeee 8),[88,88] eeeeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M),[88] ee e [8,8-eee(eeeeeeeeeeeee-8-ee)eeeeee]eeeeeeeee(MM) eeeeeee[88] eeeee eee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeee eeeeee.
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeee ee 8-Meeeeeeeeeeeeeeeeee ee ee Meeee[88]
Meeeeeeee eee eeeeeee ee eeeee eeeeeeeee eeeeeeeee, eeeeeeeeee M—M eeee eeeeeeeee eee eeee eeeeeeeee. Meee, eee eeeeeeeee ee eeeeeeeee 8-eeeeeeeeeeeeeee eeee eeeee eeeeeee eee eeeeeee eee eeee eeee eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M) eeee (M,M)-8,8′-eee[(M)-8-(eeeeeeeeeeeeeeeee)eeeee]-8,8′-eeeeeeeeeee [(M,M)-(M,M)-MeMMMM] (e.e., ee eeee 8, Meeeee 88)[88] ee eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee(M) eeee 8,8′-eee(eeeeeeeeeeeeeeeeeeeeeee)-8,8′-eeeeeeeee-8,8′-eeeeeeeeee.[88] Mee Meeeeee eeeeeeeee ee eeeeeeeeeeee ee α,β-eeeeeeeeeee eeeeee eee eeeeeeeee ee e eeeee–eeeeeeee eeeeeee eeee eeee eeeeeeeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeeeeee Meeeeee Meeeeeeee ee Meeeeeeeeeeee[88,88,88]
Meeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeee eeeeeeee eeee eeee eeeeeeeeeeeeeeee. Meeeeeeee, eeee ee eeeeeeee ee eeeeeeeeee eeeeeeeee ee eeee eeeeeeeee, eeeeeee eeeeeeeeeee 8,8-eeeeeeee, eeeeeeeeeeeeeeee, eee eeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeee eeee eeeeeee eeeeeeee. Mee eeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM)-eeeeeeeee eeeeeeee ee eeeee 8-eeeeeeeeeeeeeee ee eeeeee eeeeeeeeee eeeeeeee eeeeeee ee eeee eeeeeeeeeee ee eeee eee Meeeeee eeeeee [(M/M) 8:8] ee 88% eeeeeeee eeeee (Meeeee 88). Meeeeee eeeeeeeee eeee eee-8-ee-8-eee eeeee eee eeeeeeeeeeeee eeeeee ee 88% eeeee. Meeee eeeeeeeee eeeeeee eeeeeee eeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeee, eeeeeeeeee eeee eeeeeeee ee eee α-M—M eeee ee eeeeeeee eeeeeeee eeee eeeeee eeee eeee ee ee eeeeeeeeee M—M eeee.[88]
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeee Meeeeeee ee Meeeeeeeee Meeeeeeee[88]
M eeeeee eeeeeeeeee ee ee eeeeeeeee eeeeeeeeee eeeeee eee eee eeeeeeeee ee eeeee-eeeee eeeeeeee eeeeeeeee, eeeeeeeeee eeeee-Meeeeeee (Meeeee 88).[88–88] M eeeeeeee eeeeee eeee e eeee eeeeeee ee eeeeeeeeee eeeeee, eeee ee eeeee, eeeeeeeeeeeeee, eeeee, eee eee, eee ee eeee ee eee eeeeee Meeeeee eeeeeeee. Meee eee eeeee eeeee ee eee eeeeeeee eeeeee ee eeeeeeeee eee eee eeeeee Meeeeee eeeeeeee ee eeeeeee, eee eee eeeeee Meeeeee eeeeee eeeeee eee ee eeeee eee eeeee eeeee eeeee.[88–88]
Meeeee 88 Meeeee Meeeeeeeee Meeee ee e Meeeee Meeeeeeeeee eee Meeeeeeeeeeeee eeeee-Meeee Meeeeeee Meeeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeee 8-{[8,8-Meeeeee-8-(8-eeeee)eeeeee]eeeee}eeeeeeee (8); Meeeeee Meeeeeeee:[88]
M eeeeeee ee eeeeee 8-[(8-eeeeeeeeeeeeeeeee)eeeee]eeeeeeee (8.888 e, 8.88 eeee), 8-eeeeeeeeeeeeeeeeeee (8.888 e, 8.88 eeee), eee [MeM8(MMe8)8] (8.888 e, 8.888 eeee) ee eee MMM (8.8 eM) eee eeeeeee eeeee eeeee ee ee eee 88 e. Mee eeeee eeeeee eeee eee eeeeeeee eeeeeee ee e eeeeeeeee eee; eeeee: 8.888 e (88%).
Meeeeeeee (M)-8-Meeee-8-eeeeee-8-eeeeeeeeeeee (8); Meeeeee Meeeeeeee:[88]
Meeee e M8 eeeeeeeeee, [MeM(MM)(MMe8)8] (8.8 ee, 8.888 eeee) eee 8,8′-eee[8-(eeeeeeeeeeeeeeeee)eeeee]-8,8′-eeeeeeeeeee (MeMMMM) (8.8 ee, 8.888 eeee) eeee eeeeeeeee ee eeeeeee (MMMMMMM: eeeeeeeeee) (8 eM). Meeeeeeee 8-eeeeeeeeeeeeeee (8.8 eeee) eee eeeee, eee eee eeeeeee eee eeeeee ee 8°M. Meee MMM (8.8 eeee) eee eeeee eeeeee 8 eee, eee eee eeeeeee eee eeee eeeeeeee ee 8°M. Mee eeeeeee eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee; eeeee: 88%; ee ee. 888°M/8 Meee; 88% ee.
References
| [42] | Meeee, M.; Meee, M.; Meeeee, M.; Meeeeeeee, M.-M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [43] | Meeeeeeee, M.-M.; Meeee, M.; Meee, M.; Meeeee, M.; Meeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [63] | Meeeeeeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [71] | Meeeeeee, M.; Meeeee, M.; Meeee, M.; Meeee, M.; Meee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [72] | Meeee, M. M.; Meeee, M.; Meeeeeee, M. M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
| [73] | Meeeeeee, M.; Meeeeeeee, M.; Mee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [74] | Meeeeee, M.; Meeeee, M.; Meeeee, M., Meeeeee, (8888), 888. |
| [75] | Meeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [76] | Meeeeeee, M.; Meeeeeeee, M.; Mee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [77] | Meeeeeee, M. M., Meeeeee, (8888), 88. |
| [78] | Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [79] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
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