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2.1.1.4.1.3 Michael Reactions with Nitroalkanes

DOI: 10.1055/sos-SD-205-00001

Nagasawa, K.; Sohtome, Y.Science of Synthesis: Asymmetric Organocatalysis, (2012225.

Amidines can also be utilized as catalysts for Michael additions to nitroalkenes. In 2008, Wulff and co-workers developed the amidinethiourea 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 5594% yield with 74:26 to 90:10 syn-selectivity and 9195% ee.

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References


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