The DOI matches its Crossref record; 12 of the 12 references it cites were found in a registry or an index.
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
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
Sakthivel, K., Notz, W., Bui, T., & Barbas, C. F. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010037z · Cited by 1,166
Procter, G. (1996) · doi:10.1093/oso/9780198557265.001.0001 · Cited by 1,136
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
Catalytic Asymmetric Synthesis of anti-1,2-Diols
Notz, W., & List, B. (2000) · Journal of the American Chemical Society · doi:10.1021/ja001460v · Cited by 645
Proline-Catalyzed Asymmetric Aldol Reactions between Ketones and α-Unsubstituted Aldehydes
List, B., Pojarliev, P., & Castello, C. (2001) · Organic Letters · doi:10.1021/ol006976y · Cited by 381
Heathcock, C. H. (1984) · Asymmetric Synthesis · doi:10.1016/b978-0-12-507703-3.50007-5 · Cited by 244
Direct Catalytic Asymmetric Aldol Reaction: Synthesis of Either syn- or anti-α,β-Dihydroxy Ketones
Yoshikawa, N., Kumagai, N., Matsunaga, S., Moll, G., Ohshima, T., Suzuki, T., & Shibasaki, M. (2001) · Journal of the American Chemical Society · doi:10.1021/ja015580u · Cited by 191
Mukaiyama, T. (1982) · Organic Reactions · doi:10.1002/0471264180.or028.03 · Cited by 168
Direct Asymmetric Aldol Reactions of Acetone Using Bimetallic Zinc Catalysts
Trost, B. M., Silcoff, E. R., & Ito, H. (2001) · Organic Letters · doi:10.1021/ol0161211 · Cited by 162
ChemInform Abstract: THE DIRECTED ALDOL REACTION
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Cited by
Small-Molecule H-Bond Donors in Asymmetric Catalysis
Doyle, A. G., & Jacobsen, E. N. (2007) · Chemical Reviews · doi:10.1021/cr068373r · Cited by 2,608
In the Golden Age of Organocatalysis
Dalko, P. I., & Moisan, L. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200400650 · Cited by 2,595
Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation
Uraguchi, D., & Terada, M. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0491533 · Cited by 1,616
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
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
- 12
- FWCI
- 38.38
- Type
- journal article
- Language
- en
- Open access
- closed
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