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List-Barbas-Mannich reaction catalyzed by modularly designed organocatalysts
S. Perera, D. Sinha, , V. Trieu-Do, J.C.-G. Zhao
Published in American Chemical Society
Volume: 78
Issue: 21
Pages: 10947 - 10953
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). © 2013 American Chemical Society.
About the journal
JournalData powered by TypesetJournal of Organic Chemistry
PublisherData powered by TypesetAmerican Chemical Society