A versatile synthon for chemoselective N-acylation reagents, 2-fluoro-N-mesylaniline

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 18, 1998, Pages 2973-2974

  Kondo, Kazuhiro ^a   Sekimoto, Erika ^a   Miki, Kazuki ^a   Murakami, Yasuoki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751281778     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806186f     Document Type: Article

References (24)

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18. (a) Y. Murakami, K. Kondo, K. Miki, Y. Akiyama, T. Watanabe and Y. Yokoyama, Tetrahedron Lett., 1997, 38, 3751;
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20. enantioselective N-acetylation: K. Kondo, T. Kurosaki and Y. Murakami, Synlett, 1998, 725.
21. 2 = BnO, cyclohexyl, t-butyl) was also unsuccessful.
22. N-Acetyl and benzoyl-N-trifluoromethanesulfonylanilines have been shown to behave as acylating reagents: J. B. Hendrickson and R. Bergeron, Tetrahedron Lett., 1973, 4607. However, preparation of N-benzyloxycarbonyl-N-trifluoromethanesulfonylaniline was unsuccessful.
23. The selectivity in the acylation of a 1:1 mixture of a less hindered amine and a hindered amine was also investigated with 4b and 8b, respectively. The observed selectivity in the acylation with 4b and 8b was superior to the currently used reagents, as shown in Table 4 below. Table 4 Competition acylation. Matrix Equation Presented Table Presented
24. +), 244, 91 (bp). A satisfactory CHN analysis ±0.3% was obtained. Other compounds 5b-8b were prepared in an analogous fashion.