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Organocatalytic Direct Asymmetric Aldol Reactions in Water
Abstract
We have developed direct asymmetric cross-aldol reactions that can be performed in water without addition of organic solvents. A bifunctional catalyst with a long hydrophobic alkyl chain efficiently catalyzed the reactions and afforded the desired aldol products in excellent yield with high enantiomeric excess, even when only an equal molar ratio of the donor and acceptor was used. These results reveal an effective design strategy for the development of aqueous organocatalytic systems.
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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
Asymmetric Organocatalysis: From Infancy to Adolescence
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200704684 · Cited by 1,252
Organocatalysis Lost: Modern Chemistry, Ancient Chemistry, and an Unseen Biosynthetic Apparatus
Barbas, C. F. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200702210 · Cited by 527
Self-citationAsymmetrische Organokatalyse: Eintritt in die Reifezeit
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie · doi:10.1002/ange.200704684 · Cited by 398
Shi, F.-Q., Li, X., Xia, Y., Zhang, L., & Yu, Z.-X. (2007) · Journal of the American Chemical Society · doi:10.1021/ja071070+ · Cited by 301
Metadata
- Authors
- Mase, N., Nakai, Y., Ohara, N., Yoda, H., Takabe, K., Tanaka, F., & Barbas, C. F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-12-31
- Volume
- 128
- Issue
- 3
- Pages
- 734-735
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2075392135
- Cited by
- 653
- References
- 0
- FWCI
- 33.15
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mase, N., Nakai, Y., Ohara, N., Yoda, H., Takabe, K., Tanaka, F., & Barbas, C. F. (2006). Organocatalytic Direct Asymmetric Aldol Reactions in Water. Journal of the American Chemical Society. https://doi.org/10.1021/ja0573312
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