The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Ns strategies: a highly versatile synthetic method for amines
Abstract
A highly efficient and versatile synthetic method for amines was established using nitrobenzenesulfonamides (Ns-amides) as both a protecting and activating group. The alkylation of N-monosubstituted Ns-amides either proceeded conventionally or under Mitsunobu conditions to provide the N,N-disubstituted sulfonamides, and the Ns group was removed easily with soft nucleophiles via Meisenheimer complexes to give the corresponding secondary amines. The major advantage of this protocol is that both alkylation and deprotection proceed under mild conditions. Thus, with this methodology, the total synthesis of linear and/or macrocyclic natural polyamines can be accomplished efficiently.
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Cites
Fukuyama, T., Jow, C.-K., & Cheung, M. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)01316-a · Cited by 914
Self-citationFukuyama, T., Cheung, M., Jow, C.-K., Hidai, Y., & Kan, T. (1997) · Tetrahedron Letters · doi:10.1016/s0040-4039(97)01334-8 · Cited by 289
Self-citationSite-Selective N-Methylation of Peptides on Solid Support
Miller, S. C., & Scanlan, T. S. (1997) · Journal of the American Chemical Society · doi:10.1021/ja9635443 · Cited by 228
Cited by
The Mitsunobu reaction in the 21stcentury
Fletcher, S. (2015) · Organic Chemistry Frontiers · doi:10.1039/c5qo00016e · Cited by 290
Desulfonylation via Radical Process: Recent Developments in Organic Synthesis
Chu, X.-Q., Ge, D., Cui, Y.-Y., Shen, Z.-L., & Li, C.-J. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00084 · Cited by 259
Maeda, H., Yamamoto, K., Kohno, I., Hafsi, L., Itoh, N., Nakagawa, S., Kanagawa, N., Suzuki, K., & Uno, T. (2007) · Chemistry – A European Journal · doi:10.1002/chem.200600522 · Cited by 85
Metadata
- Authors
- Kan, T., & Fukuyama, T.
- Venue
- Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2004
- Issue
- 4
- Pages
- 353
- ISSN
- 1359-7345 (ISSN-L)
- 1364-548X
- OpenAlex
- W2119398944
- Cited by
- 511
- References
- 3
- FWCI
- 12.50
- 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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