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Asymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids
Open accessAbstract
This report describes the development of an enantioselective C-N bond-forming reaction to produce 1,2,3,4-tetrahydroisoquinoline-derived cyclic aminals catalyzed by chiral phosphate anions. Central to the success of this goal was the design of a library of 3,3'-triazolyl BINOL-derived phosphoric acids capable of forming attractive hydrogen-bonding interactions with the peptide-like substrate. We envision this work will offer an alternative to the conventional strategy of increasing catalyst steric bulk to improve enantioselectivity with BINOL-derived phosphoric acids.
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Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cited by
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Organocatalysis in Inert C–H Bond Functionalization
Qin, Y., Zhu, L., & Luo, S. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00657 · Cited by 785
Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis
Toste, F. D., Sigman, M. S., & Miller, S. J. (2017) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00613 · Cited by 257
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Metadata
- Authors
- Neel, A. J., Hehn, J. P., Tripet, P. F., & Toste, F. D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-09-11
- Volume
- 135
- Issue
- 38
- Pages
- 14044-14047
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2331335689
- Cited by
- 198
- References
- 1
- FWCI
- 12.80
- Type
- journal article
- Language
- en
- Open access
- green
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- Neel, A. J., Hehn, J. P., Tripet, P. F., & Toste, F. D. (2013). Asymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids. Journal of the American Chemical Society. https://doi.org/10.1021/ja407410b
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