Chemistry Reference
In-Depth Information
d-xylofuranose 235b and d-galactopyranose 235c gave virtually no diastereoselec-
tivity. The best result was achieved using 1,2-deoxy d-glucose derivative 235d,
which offered up to 80% de. This study highlights, once again, how strong an
impact the carbohydrate architecture may have on stereoselectivity.
References
1 Kunz, H., Müller, B., and
Schanzenbach, D. (1987) Angew. Chem.
Int. Ed. Engl. , 26 , 267.
2 Stähle, W. and Kunz, H. (1991) Synlett ,
260.
3 (a) Shing, T.K.M. and Lloyd-Williams, P.
(1987) J. Chem. Soc., Chem. Commun. ,
423; (b) Shing, T.K.M., Chow, H.-F., and
Chung, I.H.F. (1996) Tetrahedron Lett. ,
37 , 3713.
4 (a) Nouguier, R., Gras, J.-L., Giraud, B.,
and Virgili, A. (1991) Tetrahedron Lett. ,
32 , 5529; (b) Nouguier, R., Gras, J.-L.,
Giraud, B., and Virgili, A. (1992)
Tetrahedron , 48 , 6245.
5 (a) Nagatsuka, T., Yamaguchi, S.,
Totani, K., Takao, K., and Tadano, K.-I.
(2001) Synlett , 481; (b) Nagatsuka, T.,
Yamaguchi, S., Totani, K., Takao, K., and
Tadano, K. (2001) J. Carbohydr. Chem. ,
20 , 519.
6 Totani, K., Takao, K., and Tadano, K.
(2004) Synlett , 2066.
7 Ferreira, M.L.G., Pinheiro, S., Perrone,
C.C., Costa, P.R.R., and Ferreira, V.F.
(1998) Tetrahedron: Asymmetry , 9 , 2671.
8 Nouguier, R., Mignon, V., and Gras, J.-L.
(1999) J. Org. Chem. , 64 , 1412.
9 Enholm, E.J. and Jiang, S. (2000) J. Org.
Chem. , 65 , 4756.
10 (a) Sarotti, A.M., Spanevello, R.A., and
Suárez, A.G. (2004) Tetrahedron Lett. , 45 ,
8203; (b) Sarotti, A.M., Spanevello, R.A.,
and Suárez, A.G. (2005) Tetrahedron Lett. ,
46 , 6987; (c) Sarotti, A.M., Spanevello,
R.A., and Suárez, A.G. (2006) Org. Lett. ,
8 , 1487; (d) Sarotti, A.M., Spanevello,
R.A., Duhayon, C., Tuchagues, J.-P., and
Suárez, A.G. (2007) Tetrahedron , 63 , 241;
(e) Zanardi, M.M. and Suárez, A.G.A.G.
(2009) Tetrahedron Lett. , 50 , 999.
11 (a) Banks, M.R., Blake, A.J.,
Cadogan, J.I.G., Dawson, I.M., Gaur, S.,
Gosney, I., Gould, R.O., Grant, K.J., and
Hogson, P.K.G. (1993) J. Chem. Soc.,
Chem. Commun. , 1146; (b) Banks, M.R.,
Cadogan, J.I.G., Gosney, I., Gaur, S., and
Hogson, P.K.G. (1994) Tetrahedron:
Asymmetry , 5 , 2447; (c) Banks, M.R.,
Cadogan, J.I.G., Gosney, I., Gould, R.O.,
Hogson, P.K.G., and McDougall, D.
(1998) Tetrahedron , 54 , 9765.
12 Reichenstein, T. and Grüssner, A. (1934)
Helv. Chim. Acta , 17 , 311.
13 (a) Felber, H., Kresze, G., Braun, H., and
Vasella, A. (1984) Tetrahedron Lett. , 25 ,
5381; (b) Felber, H., Kresze, G., Prewo,
R., and Vasella, A. (1986) Helv. Chim.
Acta , 69 , 1137.
14 Vasella, A. (1977) Helv. Chim. Acta , 60 ,
1273.
15 Beer, D. and Vasella, A. (1985) Helv.
Chim. Acta , 68 , 2254.
16 The absolute configuration of the
hetero-Diels-Alder product of 60 with
cyclohexadiene was at first assigned
incorrectly; the correct stereochemistry
was published later by these authors:
Braun, H., Charles, R., Kresze, G.,
Sabuni, M., and Winkler, J. (1987) Liebigs
Ann. Chem. , 1129.
17 Braun, H., Felber, H., Kresze, G.,
Schmidtchen, F., Prewo, R., and
Vasella, A. (1993) Liebigs Ann. Chem. , 261.
18 Werbitzky, O., Klier, K., and Felber, H.
(1990) Liebigs Ann. Chem. , 267.
19 Schurrle, K., Beier, B., and Piepersberg,
W. (1991) J. Chem. Soc., Perkin Trans. 1 ,
2407.
20 (a) Defoin, A., Sarazin, H., Strehler, C.,
and Streith, J. (1994) Tetrahedron Lett. ,
35 , 5653; (b) Defoin, A., Sarazin, H., and
Streith, J. (1996) Helv. Chim. Acta , 79 ,
560; (c) Defoin, A., Sarazin, H., and
Streith, J. (1997) Tetrahedron , 53 , 13769;
(d) Defoin, A., Sarazin, H., Sifferlen, T.,
Strehler, C., and Streith, J. (1998) Helv.
Chim. Acta , 81 , 1417.
Search WWH ::




Custom Search