The DOI matches its Crossref record; 8 of the 8 references it cites were found in a registry or an index.
Two-Step Synthesis of Carbohydrates by Selective Aldol Reactions
Abstract
Studies of carbohydrates have been hampered by the lack of chemical strategies for the expeditious construction and coupling of differentially protected monosaccharides. Here, a synthetic route based on aldol coupling of three aldehydes is presented for the de novo production of polyol differentiated hexoses in only two chemical steps. The dimerization of α-oxyaldehydes, catalyzed by l -proline, is then followed by a tandem Mukaiyama aldol addition-cyclization step catalyzed by a Lewis acid. Differentially protected glucose, allose, and mannose stereoisomers can each be selected, in high yield and stereochemical purity, simply by changing the solvent and Lewis acid used. The reaction sequence also efficiently produces 13 C-labeled analogs, as well as structural variants such as 2-amino– and 2-thio–substituted derivatives.
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Citations
Cites
Proline-Catalyzed Direct Asymmetric Aldol Reactions
List, B., Lerner, R. A., & Barbas, C. F. (2000) · Journal of the American Chemical Society · doi:10.1021/ja994280y · Cited by 2,873
Asymmetric synthesis of bicyclic intermediates of natural product chemistry
Hajos, Z. G., & Parrish, D. R. (1974) · The Journal of Organic Chemistry · doi:10.1021/jo00925a003 · Cited by 1,252
Proline-catalyzed asymmetric reactions
List, B. (2002) · Tetrahedron · doi:10.1016/s0040-4020(02)00516-1 · Cited by 1,154
New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures
Eder, U., Sauer, G., & Wiechert, R. (1971) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197104961 · Cited by 1,057
The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes
Northrup, A. B., & MacMillan, D. W. C. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0262378 · Cited by 706
Self-citationCarbohydrates in Chemistry and Biology
Ernst, B., Hart, G. W., & Sinaý, P. (2000) · Wiley eBooks · doi:10.1002/9783527618255 · Cited by 594
Northrup, A. B., Mangion, I. K., Hettche, F., & MacMillan, D. W. C. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200453716 · Cited by 320
Self-citationMovassaghi, M., & Jacobsen, E. N. (2002) · Science · doi:10.1126/science.1076547 · Cited by 244
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
Plausible 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
Hayashi, Y., Matsuzawa, M., Yamaguchi, J., Yonehara, S., Matsumoto, Y., Shoji, M., Hashizume, D., & Koshino, H. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200601506 · Cited by 120
Metadata
- Authors
- Northrup, A. B., & MacMillan, D. W. C.
- Venue
- Science
- Published
- 2004-09-17
- Volume
- 305
- Issue
- 5691
- Pages
- 1752-1755
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2029870060
- Cited by
- 391
- References
- 8
- FWCI
- 22.67
- Type
- journal article
- Language
- en
- Open access
- closed
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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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