Fukuyama and co-workers have demonstrated various reactions using the N-substituted sulfonamide 5.3) Smooth reactions of 5 occur with alkyl halides under basic conditions and alcohols under Mitsunobu conditions to provide o-nitrobenzenesulfonyl (o-Ns) amines 6. The various o-Ns amines (Alloc, Boc, Cbz) 6 obtained from these reactions can be selectively deprotected, under the appropriate conditions, to afford the monoprotected amines 7 and 8. Furthermore, 7 can be converted to the primary amine in high yields via a second deprotection. 8 can be converted to the secondary amine in high yields by repeating the alkylation and deprotection process.4)
On the other hand, acetoxime O-(2,4,6-trimethylphenyl)sulfonate 9 has been reported as a useful electrophilic aminating agent. 9 reacts with Grignard reagents in the presence of a catalytic amount of magnesium chloride to afford primary amines in good yields.5)
- 1)a) S. Gabriel, Ber. 1887, 20, 2224.
- 2)a) J. D. Elliott, J. H. Jones, J. Chem. Soc., Chem. Commun. 1977, 758.
- 3)T. Fukuyama, M. Cheung, T. Kan, Synlett 1999, 1301.
- 4)T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron 2002, 58, 6267.
- 5)E. Erdik, M. Ay, Synth. React. Inorg. Met.-Org. Chem. 1989, 19, 663.
Artikel #: B2857 | Zuiverheid >95.0%(HPLC)(N)
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