The DOI matches its Crossref record; 12 of the 12 references it cites were found in a registry or an index.
A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones with Aldedydes
Abstract
L-proline amides derived from various chiral beta-amino alcohols that bear substituents with various electron natures at their stereogenic centers are prepared and evaluated for catalyzing the direct Aldol reaction of 4-nitrobenzaldehyde with acetone. Catalysts with strong electron-withdrawing groups are found to exhibit higher catalytic activity and enantioselectivity than their analogues with electron-donating groups. The presence of 2 mol % catalyst 4g significantly catalyzes the direct Aldol reactions of a wide range of aldehydes with acetone and butanone, to give the beta-hydroxy ketones with very high enantioselectivities ranging from 96% to >99% ee. High diastereoselectivity of 95/5 was observed for the anti Aldol product from the reaction of cyclohexanone, and excellent enantioselectivity of 93% ee was provided for anti Aldol product from the reaction of cyclopentanone.
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Citations
Cites
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Cited by
Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Nonlinear Effects in Asymmetric Catalysis
Satyanarayana, T., Abraham, S., & Kagan, H. B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200705241 · Cited by 591
Chiral Metal–Organic Frameworks
Gong, W., Chen, Z., Dong, J., Liu, Y., & Cui, Y. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00740 · Cited by 579
Highly Diastereo‐ and Enantioselective Direct Aldol Reactions in Water
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Solvent‐Free Carbon‐Carbon Bond Formations in Ball Mills
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Metadata
- Authors
- Tang, Z., Yang, Z.-H., Chen, X.-H., Cun, L.-F., Mi, A.-Q., Jiang, Y.-Z., & Gong, L.-Z.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-06-01
- Volume
- 127
- Issue
- 25
- Pages
- 9285-9289
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2155665819
- Cited by
- 386
- References
- 12
- FWCI
- 22.43
- Type
- journal article
- Language
- en
- Open access
- closed
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