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Please login to access the full content or check if you have access via2.1.1.4.1 Catalytic Asymmetric Michael Reactions
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Nagasawa, K.; Sohtome, Y., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 20.
Catalytic asymmetric 1,4-addition (Michael) reactions are useful tools for the preparation of nitrogen-containing chiral building blocks.[28–30] Among the currently available methods, asymmetric organocatalytic conjugate additions to nitroalkenes have received great attention as a result of their reactivity and versatility. In 2006, Terada and co-workers reported the results of their initial studies leading to the development of the axially chiral guanidine catalyst (R)-53 (Scheme 20) for catalytic asymmetric Michael reactions of 1,3-dicarbonyl compounds 55 with nitroalkenes 54 to give products 56.[6,31]
Me eee ee eeee ee Meeeee 88, eeeeeeeee (M)-88, eeeee eeeeeeeee eee eeeee 8,8-eee(8,8-ee-eeee-eeeeeeeeeee)eeeeee eeeeeeeeeee, eeeeeeee eee eeeeeeee ee e eeeee eeeee ee eeeeeeeeeeee 88 eeee eeee eeeeeeeeee ee eeeee ee eeeeeeeee eeeeeeee eee eeeeeeeeeeeeeeeeee. Meeeeeeee eeee eeeeeeee eeeeee eee eeeeeeeeeeeeeeeeeeee eee eeeeeeee eee e eeeeeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee 88 eeee eeeeeeeeee eeeeeeeee 88. Meeeeeee (M)-88 eeee eeeeeeee eeee eeeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeee eeeeeeeeeeee, eeeee eee eeeeeeeeeee eeeeeeeeee ee eeeee ee eeeeeeeeee eee eeeeeeeeeee. Meeeeeee eeeeeeeee eeeeeeeeeeee eeee eeeeeeee eeeee eeeeeeeeeeeeeeeeeeee eeee eeeee eeeeeeee eeeeeeeeeeee, eee eeeeeeeee eeeeeee ee eeeeeeeeee ee e eeeeeeeeee eeee eeee e eeeeeeee eeeeeee ee 8 eee% ee eeee. Meeeeee eeeee ee 8,8-eeeeeeeeee eeeeeeeee eeee eeeeeeeeeee ee eeeeeeeee eeeeeeee ee eeee eeeeeeeee eeeeee. Meeeeeeee eeeeee (88–88%) eee eeee eeeeeeeeeeeeeeeeeeee (88–88% ee) ee eee β-eeeeeeee ee eee eeeee eeeee eee eeeeeeee ee eeeeeeeee ee α-eeeeeeeeeee eeeeeeeee, 8,8-eeeeeeeee, eee β-eeee eeeeee.
Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeee Meeeeeeee ee Meeeeeeeeeee eeee 8,8-Meeeeeeeee Meeeeeeee Meeee e Meeeee Meeeeeeee Meeeeeee[8,88]
M8 | M8 | M8 | M8 | 88 (eee%) | Meeeeee | Meee (e) | Meeee (%) | ee (%) | Mee |
---|---|---|---|---|---|---|---|---|---|
Me | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
Me | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
Me | MeMe | MeMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeMM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-M8MM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeMM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeMM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-MeM8M8 | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-eeeee | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
8-eeeeeeee | MMe | MMe | M | 8 | Me8M | 8 | 88 | 88 | [88] |
eMe | MMe | MMe | M | 8 | eMe8M | 88 | 88 | 88 | [88] |
eMe | MMe | MMe | M | 8 | eMe8M | 88 | 88 | 88 | [88] |
Me | MMe | MMe | M | 8 | eMe8M | 88 | 88 | 88 | [88] |
Me | MMe | MMe | Me | 8 | Me8M | 88 | 88 | 88 | [88] |
Me | Me | Me | M | 8 | Me8M | 8 | 88 | 88 | [88] |
Me | Me | MMe | M | 8 | eMe8M | 8 | 88 | 88e | [88] |
e ee 8:8; eeee eeeeeeeeeeeee eee 88% ee.
Meeeeeeeeeee Meeeeeeee
Meeeeeee 8-(8-Meeee-8-eeeeeeeeeee)eeeeeeee (88, M8 = Me; M8 = M8 = MMe; M8 = M); Meeeeee Meeeeeeee:[88]
Me e eeee ee (M)-8-eeeee-8-eeeeeeeeeeee (88, M8 = Me; 88.8 ee, 8.88 eeee) eee eeeeeeee eeeeeeee (88, M8 = M8 = MMe; M8 = M; 88.8 µM, 8.88 eeee) ee Me8M (8.8 eM) eee eeeee (M)-88 (8.88 ee, 8.888 eeee) ee −88 °M. Mee eeeeeeeee eeeeeee eee eeeeeee eee 8 e eee eeee eeeeeee eeee eeeee MMe ee MeMM (8:88; e eee eeeee). Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee e eeeeeee, eeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee/Me8M 8:8 ee 8:8); eeeee: eeeee.
References
[6] | Meeeee, M., M. Meeee. Mee. Meee., Mee., (8888) 88, 8888. |
[28] | Meeeeeee, M. M., Mee. M. Mee. Meee., (8888), 8888. |
[29] | Meeeşe, M.; Meeeee, M. M.; Máeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 888. |
[30] | Meeeeee, M. M.; Meeíe, M.; Meeeeeee, M., Meeeeeeee, (8888), 8888. |
[31] | Meeeee, M.; Mee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |