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Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation
Abstract
It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines. The beneficial effects of the 3,3'-bisaryl substituents of the catalysts on the enantioselectivity are greatly appreciated, and thus 1d functions as an excellent catalyst. The Brønsted acid-catalyzed direct Mannich reactions presented herein provide an attractive way to construct beta-aminoketones under extremely mild conditions. The stereochemical course of this reaction was established through the synthesis of Boc-(S)-phenylglycine methylester. The transformation thus demonstrated is applicable to a useful method for the synthesis of various phenylglycine derivatives.
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Citations
Cited by
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Enantioselective amine α-functionalization via palladium-catalysed C–H arylation of thioamides
Jain, P., Verma, P., Xia, G., & Yu, J.-Q. (2017) · Nature Chemistry · doi:10.1038/nchem.2619 · Cited by 336
Asymmetrische Gegenanionen‐vermittelte Katalyse: Konzept, Definition und Anwendungen
Mahlau, M., & List, B. (2013) · Angewandte Chemie · doi:10.1002/ange.201205343 · Cited by 313
Metadata
- Authors
- Uraguchi, D., & Terada, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-04-09
- Volume
- 126
- Issue
- 17
- Pages
- 5356-5357
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2169174125
- Cited by
- 1,616
- References
- 0
- FWCI
- 31.35
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation. https://app.cochat.ai/papers/10.1021/ja0491533
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- Uraguchi, D., & Terada, M. (2004). Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation. Journal of the American Chemical Society. https://doi.org/10.1021/ja0491533
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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