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Enantioselective Organocatalytic Direct Aldol Reactions of α‐Oxyaldehydes: Step One in a Two‐Step Synthesis of Carbohydrates
Open accessAbstract
Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereocontrolled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.
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Citations
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
Asymmetrische Organokatalyse: Eintritt in die Reifezeit
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie · doi:10.1002/ange.200704684 · Cited by 398
Two-Step Synthesis of Carbohydrates by Selective Aldol Reactions
Northrup, A. B., & MacMillan, D. W. C. (2004) · Science · doi:10.1126/science.1101710 · Cited by 391
Self-citationPlausible origins of homochirality in the amino acid catalyzed neogenesis of carbohydrates
Córdova, A., Engqvist, M., Ibrahem, I., Casas, J., & Sundén, H. (2005) · Chem. Commun. · doi:10.1039/b500589b · Cited by 127
Metadata
- Authors
- Northrup, A. B., Mangion, I. K., Hettche, F., & MacMillan, D. W. C.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2004-04-06
- Volume
- 43
- Issue
- 16
- Pages
- 2152-2154
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2169392145
- Cited by
- 320
- References
- 0
- FWCI
- 23.51
- Type
- journal article
- Language
- en
- Open access
- bronze
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- Northrup, A. B., Mangion, I. K., Hettche, F., & MacMillan, D. W. C. (2004). Enantioselective Organocatalytic Direct Aldol Reactions of α‐Oxyaldehydes: Step One in a Two‐Step Synthesis of Carbohydrates. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.200453716
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