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