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List–Barbas–Mannich Reaction Catalyzed by Modularly Designed Organocatalysts

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journal contribution
posted on 01.11.2013, 00:00 by Sandun Perera, Debarshi Sinha, Nirmal K. Rana, Van Trieu-Do, John Cong-Gui Zhao
The List–Barbas–Mannich reaction of ethyl (p-methoxyphenylimino)­acetate (p-methoxyphenyl = PMP) with unmodified aldehydes or ketones catalyzed by modularly designed organocatalysts (MDOs) that are self-assembled from proline and cinchona alkaloid thioureas (such as a quinidine-derived thiourea) produces the corresponding γ-oxo-α-amino acid derivatives in high yields and excellent stereoselectivities. No solvent is necessary for this reaction. Aldehydes are especially good substrates for this reaction: The reaction takes only a few minutes to yield the corresponding List–Barbas–Mannich products in excellent dr (up to >99:1) and ee values (up to >99% ee).