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The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes
Abstract
The first enantioselective catalytic direct cross-aldol reaction that employs nonequivalent aldehydes has been accomplished using proline as the reaction catalyst. Structural variation in both the aldol donor (R1 = Me, n-Bu, Bn, 91 to >99%) and aldol acceptor (R2 = I-Pr, I-Bu, c-C6H11, Et, Ph, 97-99% ee) are possible while maintaining high reaction efficiency (75-88% yield). Significantly, this new aldol variant allows facile enantioselective access to a broad range of beta-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.
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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
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
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-08
- Volume
- 124
- Issue
- 24
- Pages
- 6798-6799
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2045154252
- Cited by
- 706
- References
- 0
- FWCI
- 38.38
- Type
- journal article
- Language
- en
- Open access
- closed
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