Abstract
Sulfonamides are routinely employed as nitrogen protecting groups in organic synthesis. They are often crystalline, chemically robust, and, most importantly, the basicity/nucleophilicity of the nitrogen atom is reduced dramatically due to the presence of the electron-withdrawing sulfonyl moiety. Unlike their carbamate or amide analogues, there are no spectroscopic problems associated with rotamers when employing sulfonamides as protecting group.
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Hong AW, Cheng T-H, Raghukuma V, Sha C-K (2008) J Org Chem 73:7580
Nakanishi M, Mori M (2003) Angew Chem Int Ed 41:1934
Tomooka K, Suzuki M, Shimada M, Yanagitsura S-I, Uehara K (2006) Org Lett 8:963
Parker KA, Fokas D (1992) J Am Chem Soc 114:9688
Evans P, McCabe T, Morgan BS, Reau S (2004) Org Lett 7:43
White RD, Wood JL (2001) Org Lett 3:1825
Lee GH, Youn IK, Choi EB, Lee HK, Yon GH, Yang HC, Pak CS (2004) Curr Org Chem 8:1263
Larghi EL, Kaufman TS (1997) Tetrahdron Lett 38:3159
Moore JA, Rahm M (1961) J Org Chem 26:1109
Ankner T, Hilmersson G (2009) Org Lett 11:503
Kovacs J, Ghatak UR (1966) J Org Chem 31:119
Closson WD, Ji S, Schulenberg S (1970) J Am Chem Soc 93:650
Evans P (2007) J Org Chem 72:1830
Zeng W, Chemler SR (2008) J Org Chem 73:6045
Bunnett JF, Jenvey J (1996) J Org Chem 61:8069
Xu F, Murry JA, Simmons B, Corley E, Fitch K, Karady S, Tschaen D (2006) Org Lett 8:3885
Tamura O, Yanagimachi T, Ishibashi H (2003) Tetrahedron Asymmetry 14:3033
Young IS, Baran PS (2009) Nat Chem 1:193
Mori M, Kuroda S, Zhang CS, Sato Y (1997) J Org Chem 62:3263
Nishikawa T, Asai M, Ohyabu N, Isobe M (1998) J Org Chem 63:188
Overman LE, Carpenter NE (2005) Org React 66:1
Grigg R, Santhakumar V, Sridharan V, Thornton-Pett M, Bridge AW (1993) Tetrahedron 49:5177
Kim S, Lee T, Lee E, Lee J, Fan G-J, Lee SK, Kim D (2004) J Org Chem 69:3144
Kelleher S, Quesne P-Y, Evans P (2009) Beilstein J Org Chem 5. doi:10.3762/bjoc.5.69
Sankaranarayanan S, Chattopadhyay S (1998) Tetrahedron Asymmetry 9:2627
Krow GR (2004) Org React 43:251
Evarts JB Jr, Fuchs PL (2001) Tetrahedron Lett 42:3673
Chida N, Sugihara K, Amano S, Ogawa S (1997) J Chem Soc Perkin Trans 1:275
Song ZL, Wang BM, Tu YQ, Fan CA, Zhang SY (2003) Org Lett 5:2319
Zhoa YH, Zhoa YY, Liang LL, Yang XD, Du FX, Li LA, Zhang HB (2009) Org Lett 11:555
Capps TM, Hargrave KD, Jeffs PW, McPhail AT (1977) J Chem Soc Perkin Trans 2:1098
Sanchez IH, Larraza MI, Flores HJ, Rojas I, Alcalá R (1983) Synth Commun 13:35
Nieuwenhuis JJ, Strelow F, Strauss HF, Wiechers AJ (1981) Chem Soc Perkin Trans 1:284
Jeffs PW, Cortese NA, Wolfram J (1982) J Org Chem 47:3881
Stevens RV, Lai JT (1972) J Org Chem 37:2138
Rodgriguez R, Ollivier C, Santelli M (2004) Tetrahedron Lett 45:2289
D’Souza AM, Paknikar SK, Dev V, Beauchamp PS, Kamat SP (2004) J Nat Prod 67:700
Hanuš LO, Tchilibon S, Ponde DE, Breuer A, Fride E, Mechoulam R (2005) Org Biomol Chem 3:1116
Trost BM, Verhoeven TR, Fortunak JM (1979) Tetrahedron Lett 25:2301
Park JB, Ko SH, Kim BG, Hong WP, Lee K-J (2004) Bull Korean Chem Soc 25:27
Oehlschlager AC, Mishra P, Dhami S (1984) Can J Chem 62:791
Deardorff DR, Shambayati S, Linde RG, Dunn MM (1988) J Org Chem 53:189
Deardorff DR, Myles DC, MacFerrin KD (1985) Tetrahedron Lett 26:5615
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Geoghegan, K. (2014). Double Reduction of Cyclic Aromatic Sulfonamides. In: Selectivity in the Synthesis of Cyclic Sulfonamides. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-10338-9_5
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DOI: https://doi.org/10.1007/978-3-319-10338-9_5
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