Practical Synthesis of Sultams via Sulfonamide Dianion Alkylation: Application to the Synthesis of Chiral Sultams

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4175-4177

  Lee, Jaemoon ^a   Zhong, Yong Li ^a   Reamer, Robert A ^a   Askin, David ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONAMIDE;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; MOLECULAR DYNAMICS;

EID: 0344082863     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0356183     Document Type: Article

References (32)

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13. For the electrophilic fluorinating agent, see: (f) Differding, E.; Lang, R. W. Helv. Chem. Acta 1989, 72, 1248. (g) Differding, E.; Lang, R. W. Tetrahedron Lett. 1991, 32, 1779. (h) Takeuchi, Y.; Suzuki, T.; Satoh, A.; Shiragami, T. Shibata, N. J. Org. Chem, 1999, 64, 5708. (i) Liu, Z. Shibata, N. Takeuchi, Y. J. Org. Chem. 2000, 65, 7583.
14. For the electrophilic fluorinating agent, see: (f) Differding, E.; Lang, R. W. Helv. Chem. Acta 1989, 72, 1248. (g) Differding, E.; Lang, R. W. Tetrahedron Lett. 1991, 32, 1779. (h) Takeuchi, Y.; Suzuki, T.; Satoh, A.; Shiragami, T. Shibata, N. J. Org. Chem, 1999, 64, 5708. (i) Liu, Z. Shibata, N. Takeuchi, Y. J. Org. Chem. 2000, 65, 7583.
15. For the electrophilic fluorinating agent, see: (f) Differding, E.; Lang, R. W. Helv. Chem. Acta 1989, 72, 1248. (g) Differding, E.; Lang, R. W. Tetrahedron Lett. 1991, 32, 1779. (h) Takeuchi, Y.; Suzuki, T.; Satoh, A.; Shiragami, T. Shibata, N. J. Org. Chem, 1999, 64, 5708. (i) Liu, Z. Shibata, N. Takeuchi, Y. J. Org. Chem. 2000, 65, 7583.
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26. For the sultam synthesis via intramolecular monoanion alkylation of N-protected sulfonamide, see: (a) Kobayashi, M.; Okahara, M.; Komori, S.; Agawa, T. Synthesis 1973, 667.
27. Although a sulfonamide N,C-dianion alkylation is known for substituted sulfonamide synthesis, this intramolecular dianion alkylation method has not been exploited for the cyclic sulfonamide formation. For examples of sulfonamide or sultam dianion, see: (a) Thompson, M. E. J. Org. Chem. 1984, 49, 1700. (b) Watanabe, H.; Hauser, C. R. J. Org. Chem. 1968, 33, 4278. (c) Miller, R. A.; Humphrey, G. R.; Lieberman, D. R.; Ceglia, S. S.; Kennedy, D. J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 2000, 65, 1399. (d) Szymonika, M. J.; Heck, J. V. Tetrahedron Lett. 1989, 30, 2873.
28. Although a sulfonamide N,C-dianion alkylation is known for substituted sulfonamide synthesis, this intramolecular dianion alkylation method has not been exploited for the cyclic sulfonamide formation. For examples of sulfonamide or sultam dianion, see: (a) Thompson, M. E. J. Org. Chem. 1984, 49, 1700. (b) Watanabe, H.; Hauser, C. R. J. Org. Chem. 1968, 33, 4278. (c) Miller, R. A.; Humphrey, G. R.; Lieberman, D. R.; Ceglia, S. S.; Kennedy, D. J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 2000, 65, 1399. (d) Szymonika, M. J.; Heck, J. V. Tetrahedron Lett. 1989, 30, 2873.
29. Although a sulfonamide N,C-dianion alkylation is known for substituted sulfonamide synthesis, this intramolecular dianion alkylation method has not been exploited for the cyclic sulfonamide formation. For examples of sulfonamide or sultam dianion, see: (a) Thompson, M. E. J. Org. Chem. 1984, 49, 1700. (b) Watanabe, H.; Hauser, C. R. J. Org. Chem. 1968, 33, 4278. (c) Miller, R. A.; Humphrey, G. R.; Lieberman, D. R.; Ceglia, S. S.; Kennedy, D. J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 2000, 65, 1399. (d) Szymonika, M. J.; Heck, J. V. Tetrahedron Lett. 1989, 30, 2873.
30. Although a sulfonamide N,C-dianion alkylation is known for substituted sulfonamide synthesis, this intramolecular dianion alkylation method has not been exploited for the cyclic sulfonamide formation. For examples of sulfonamide or sultam dianion, see: (a) Thompson, M. E. J. Org. Chem. 1984, 49, 1700. (b) Watanabe, H.; Hauser, C. R. J. Org. Chem. 1968, 33, 4278. (c) Miller, R. A.; Humphrey, G. R.; Lieberman, D. R.; Ceglia, S. S.; Kennedy, D. J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 2000, 65, 1399. (d) Szymonika, M. J.; Heck, J. V. Tetrahedron Lett. 1989, 30, 2873.
31. Trecourt, F.; Mallet, M.; Marsais, F.; Queguiner, G. J. Org. Chem. 1988, 53, 1367.
32. After N,O-bis-methanesulfonylation of amino alcohol, an attempted one-pot halogenation with resulting triethylamine-HCl salt under THF or MEK reflux was not effective. N-Protected β-halosulfonamide has been prepared via N,O-bis-sulfonation followed by halide displacement: Bland, D.; Hart, D. J. ; Lacoutiere, S. Tetrahedron 1997, 53, 8871.