Abstract
The regioselective Mitsunobu alkylation of saccharin with various alcohols has been examined. The N/O-alkylation is dependent on the steric hindrance of the alcohols, that is, less sterically hindered alcohol preferentially afford N-alkylated saccharin and vice versa.
References
1.
Gençer N.
,
Demir D.
,
Sonmez F.
, and
Kucukislamoglu M.
, Bioorg. Med. Chem. , 2012 , 20 , 2811 .
2.
Zia-ur-Rehman M.
,
Choudary J.A.
,
Elsegood M.R.J.
,
Siddiqui H.L.
, and
Khan K.M.
, Eur. J. Med. Chem. , 2009 , 44 , 1311 .
3.
But T.Y.S.
, and
Toy P.H.
, Chem. Asian. J. , 2007 , 2 , 1340 .
4.
Swamy K.C.K.
,
Kumar N.N.B.
,
Balaraman E.
, and
Kumar K.V.P.P.
, Chem. Rev. , 2009 , 109 , 2551 .
5.
Robinson R.I.
,
Fryatt R.
,
Wilson C.
, and
Woodward S.
, Eur. J. Org. Chem. , 2006 , 4483 .
6.
Wang X.L.
,
Ju T.T.
,
Li X.D.
, and
Cao X.P.
, Synlett , 2010 , 19 , 2947 .
7.
Almeida R.
,
Gómez-Zavaglia A.
,
Kaczor A.
,
Cristiano M.L.S.
,
Eusébio M.E.S.
,
Maria T.M.R.
, and
Fausto R.
, Tetrahedron , 2008 , 64 , 3296 .
8.
Gómez-Zavaglia A.
,
Kaczor A.
,
Almeida R.
,
Cristiano M.L.S.
,
Eusébio M.E.S.
,
Maria T.M.R.
,
Mobili P.
, and
Fausto R.
, J. Phys. Chem. A , 2009 , 113 , 3517 .
9.
Rice H.L.
, and
Pettit G.R.
, J. Am. Chem. Soc. , 1954 , 76 , 302 .
10.
Perez C.F.
,
Calandri E.L.
,
Mazzieri M.R.
,
Arguello B.
,
Suarez A.R.
, and
Fumarola M.J.
, Org. Prep. Proc. Int. , 1984 , 16 , 37 .