Synthesis of α-fluorosulfonamides by electrophilic fluorination

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4285-4288

  Hill, Bryan ^a   Liu, Yong ^a   Taylor, Scott D ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONAMIDE;

ARTICLE; ESTERIFICATION; FLUORINATION; MOLECULAR DYNAMICS; MOLECULAR MODEL;

EID: 9444267656     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048249z     Document Type: Article

References (19)

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7. Compound 3 and other aryl sulfamates are potent irreversible inhibitors of ES. For a discussion on the mechanism of inhibition of ES by sulfamates, see: Ahmed, S.; Owen, C. P.; James, K.; Patel, C. K.; Sampson, L. J. Steroid Biochem. Mol. Biol. 2002, 80, 429-440.
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14. For example see: Thompson, M. E. J. Org. Chem. 1984, 49, 1700-1703.
15. Under these conditions, except using MeI as electrophile, we could readily α-methylate secondary sulfonamides in 60-70% yields.
16. Differding, E.; Duthaler, R. O.; Kreiger, A.; Ruegg, G. M.; Schmit, C. Synlett 1991, 395-396.
17. Lee, J.; Zhong, Y.-L.; Reamer, R. A.; Askin, D. Org. Lett. 2003, 5, 4175-4177.
18. 19F NMR's obtained from the crude reaction mixtures from the fluorination of compounds 47 and 48 suggested that similar byproducts were formed during the fluorination of 47 and 48. However, we were unable to isolate these byproducts in pure form to confirm this. These results may account for the lower yields obtained with the alkyl derivatives compared to the benzylic derivatives.
19. Inhibition studies with compound 2 and ES will be reported elsewhere.