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Please login to access the full content or check if you have access via2.1.1.4.1.3 Michael Reactions with Nitroalkanes
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Nagasawa, K.; Sohtome, Y., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 25.
Amidines can also be utilized as catalysts for Michael additions to nitroalkenes. In 2008, Wulff and co-workers developed the amidine–thiourea organocatalyst 65 for catalytic Michael reactions of nitroalkanes 66 and nitroalkenes 67.[34] An interesting feature of 65 is that it contains a dimethylamino moiety, which enhances the Brønsted basicity of the amidine group. As the results in Scheme 24 show, the methodology based on 65 is applicable to a range of nitroalkenes that bear an aromatic substituent at the β-position to produce the corresponding Michael adducts 68 in 55–94% yield with 74:26 to 90:10 syn-selectivity and 91–95% ee.
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Me | 8-MeMM8M8 | 88 | 88 | 88:88 | 88 | [88] |
Me | 8-Mee | 88 | 88 | 88:88 | 88 | [88] |
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Me | 8-MeM8M8 | 88 | 88 | 88:88 | 88 | [88] |
Me | 8-MeM8M8 | 88 | 88 | 88:88 | 88 | [88] |
Me | 8-MeM8M8 | 88 | 88 | 88:88 | 88 | [88] |
Me | 8-MeM8M8 | 88 | 88 | 88:88 | 88 | [88] |
Me | Me | 88 | 88 | 88:88 | 88 | [88] |
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References
[34] | Meeeeeeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |