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Enantioselective Direct Aza Hetero-Diels−Alder Reaction Catalyzed by Chiral Brønsted Acids
Abstract
[Structure: see text] The first chiral Brønsted acid-catalyzed asymmetric direct aza hetero-Diels-Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for the reaction of cyclohexenone with N-PMP-benzaldimine. A chiral phosphoric acid, derived from 3,3-di(4-chloropheneyl)-H8-binol, exhibited superior enantioselectivity, affording fairly good yields and enantioselectivities for the reaction of a range of aromatic aldimines with cyclohexenone.
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Cited by
Akiyama, T. (2007) · Chemical Reviews · doi:10.1021/cr068374j · Cited by 2,311
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011) · Chemical Reviews · doi:10.1021/cr100204f · Cited by 988
Prediction of higher-selectivity catalysts by computer-driven workflow and machine learning
Zahrt, A. F., Henle, J. J., Rose, B. T., Wang, Y., Darrow, W. T., & Denmark, S. E. (2019) · Science · doi:10.1126/science.aau5631 · Cited by 683
Simón, L., & Goodman, J. M. (2008) · Journal of the American Chemical Society · doi:10.1021/ja800793t · Cited by 295
Metadata
- Authors
- Liu, H., Cun, L.-F., Mi, A.-Q., Jiang, Y.-Z., & Gong, L.-Z.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-11-24
- Volume
- 8
- Issue
- 26
- Pages
- 6023-6026
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2082090466
- Cited by
- 165
- References
- 0
- FWCI
- 11.76
- Type
- journal article
- Language
- en
- Open access
- closed
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- Liu, H., Cun, L.-F., Mi, A.-Q., Jiang, Y.-Z., & Gong, L.-Z. (2006). Enantioselective Direct Aza Hetero-Diels−Alder Reaction Catalyzed by Chiral Brønsted Acids. Organic Letters. https://doi.org/10.1021/ol062499t
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