Abstract
Sulfonamides are well known motifs in medicinal chemistry, forming a large family of antibacterial agents as well as being found in numerous other drugs. The chemistry of this functional group, however, is less well documented. This review seeks to bring together the various applications and advantages of this motif in organic synthesis, which includes the sulfonamide as an activating group, protecting group, leaving group and as a molecular scaffold.
References
1.
Navia M.
, Science , 2000 , 287 , 1960 .
2.
Campbell M.M.
, and
Johnson G.
, Chem. Rev. , 1978 , 78 , 65 .
3.
Liskamp R.M.J.
,
van Ameijde J.
, and
Slot T.K.
, Tetrahedron – Asymmetry , 2010 , 21 , 469 .
4.
Biswas D.
,
Samp L.
, and
Ganguly A.K.
, Tetrahedron Lett. , 2010 , 51 , 2681 .
5.
Reddick J.J.
,
Cheng J.
, and
Roush W.R.
, Org. Lett. , 2003 , 5 , 1967 .
6.
Bordwell F.G.
, and
Cooper G.D.
, J. Am. Chem. Soc. , 1952 , 74 , 1058 .
7.
Bordwell F.G.
, and
Brannen W.T.
Jr.
, J. Am. Chem Soc. , 1964 , 86 , 4645 .
8.
Bors D.A.
, and
Streitwieser A.
Jr.
, J. Am. Chem. Soc. , 1986 , 108 , 1397 .
9.
Kenner G.W.
,
McDermott J.R.
, and
Sheppard R.C.
, Chem. Commun. , 1971 , 636 .
10.
Heidler P.
, and
Link A.
, Bioorg. Med. Chem. , 2005 , 13 , 585 .
11.
Waladau E.
, and
Pütter R.
, Angew. Chem. Int Ed. , 1972 , 11 , 826 .
12.
Loven R.
, and
Speckamp W.N.
, Tetrahedron Lett. , 1972 , 13 , 1567 .
13.
Pennell A.M.K.
, and
Motherwell W.B.
, JCS Chem. Commun. , 1991 , 877 .
14.
Tada M.
,
Shijima H.
, and
Nakamura M.
, Org. Biomol. Chem. , 2003 , 1 , 2499 .
15.
Hellwinkel D.
, and
Supp M.
, Angew. Chem. Int. Ed. , 1974 , 13 , 270 .
16.
Roy A.K.
, J. Am. Chem. Soc. , 1993 , 115 , 2598 .
17.
Beaver K.A.
,
Siegmund A.C.
, and
Spear K.L.
, Tetrahedron Lett. , 1996 , 37 , 1145 .
18.
Milburn R.R.
, and
Snieckus V.
, Angew. Chem. Int. Ed. , 2004 , 43 , 888 .
19.
Plietker B.
,
Seng D.
,
Fröhlich R.
, and
Metz P.
, Tetrahedron , 2000 , 56 , 873 .
20.
Rogatchov V.O.
,
Bernsmann H.
,
Schwab P.
,
Fröhlich R.
,
Wibbeling B.
, and
Metz P.
, Tetrahedron Lett. , 2002 , 43 , 4753 .
21.
Rogatchov V.O.
,
Merten S.
,
Seiser T.
,
Kataeva O.
, and
Metz P.
, Tetrahedron Lett. , 2008 , 49 , 133 .
22.
Aumaitre G.
,
Chanet-Ray J.
,
Durand J.
,
Vessiere R.
, and
Lonchambon G.
, Synthesis , 1983 , 10 , 816 .
23.
Chudasama V.
, and
Wilden J.D.
, Chem. Commun. , 2008 , 3768 .