-
3
-
-
0030988976
-
-
(c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492-1493.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 1492-1493
-
-
Ruble, J.C.1
Latham, H.A.2
Fu, G.C.3
-
4
-
-
0030961223
-
-
(d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 3169-3170
-
-
Kawabata, T.1
Nagato, M.2
Takasu, K.3
Fuji, K.4
-
5
-
-
0032564916
-
-
(e) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629-1630.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 1629-1630
-
-
Miller, S.J.1
Copeland, G.T.2
Papaioannou, N.3
Horstmann, T.E.4
Ruel, E.M.5
-
8
-
-
0034605437
-
-
(h) Chen, Y.; Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542-9543.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9542-9543
-
-
Chen, Y.1
Tian, S.-K.2
Deng, L.3
-
9
-
-
0034795145
-
-
Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499-1505.
-
(2001)
Synlett
, pp. 1499-1505
-
-
Vedejs, E.1
Daugulis, O.2
MacKay, J.A.3
Rozners, E.4
-
11
-
-
0041878745
-
-
(k) France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985-3012.
-
(2003)
Chem. Rev.
, vol.103
, pp. 2985-3012
-
-
France, S.1
Guerin, D.J.2
Miller, S.J.3
Lectka, T.4
-
12
-
-
32744460211
-
-
Olavi, P.; Virtanen, I.; Koppela, J. Suom. Kemistil. B 1968, 41, 326-330.
-
(1968)
Suom. Kemistil. B
, vol.41
, pp. 326-330
-
-
Olavi, P.1
Virtanen, I.2
Koppela, J.3
-
13
-
-
0001425763
-
-
For the use of sulfoxide ligands in metal-centered catalysis, see: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927-3932.
-
(1977)
Can. J. Chem.
, vol.55
, pp. 3927-3932
-
-
James, B.R.1
McMillan, R.S.2
-
14
-
-
0011941024
-
-
(b) Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. J. Org. Chem. 1991, 56, 5808-5811.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 5808-5811
-
-
Grennberg, H.1
Gogoll, A.2
Bäckvall, J.-E.3
-
15
-
-
0027511189
-
-
(c) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 123-126
-
-
Khiar, N.1
Fernández, I.2
Alcudia, F.3
-
16
-
-
0027477936
-
-
(d) Carreño, M. C.; Ruano, J. L. G.; Maestro, M. C.; Cabrejas, L. M. M. Tetrahedron: Asymmetry 1993, 4, 727-734.
-
(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 727-734
-
-
Carreño, M.C.1
Ruano, J.L.G.2
Maestro, M.C.3
Cabrejas, L.M.M.4
-
17
-
-
0030249750
-
-
(e) Ordoñez, M.; Guerrero-de la Rosa, V.; Labastida, V.; Llera, J. M. Tetrahedron: Asymmetry 1996, 7, 2675-2686.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 2675-2686
-
-
Ordoñez, M.1
Guerrero-De La Rosa, V.2
Labastida, V.3
Llera, J.M.4
-
18
-
-
0031562425
-
-
(f) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843-3848.
-
(1997)
Tetrahedron
, vol.53
, pp. 3843-3848
-
-
Chelucci, G.1
Berta, D.2
Saba, A.3
-
20
-
-
0034685980
-
-
(h) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3010-3017
-
-
Petra, D.G.I.1
Kamer, P.C.J.2
Spek, A.L.3
Schoemaker, H.E.4
Van Leeuwen, P.W.N.M.5
-
21
-
-
0034733714
-
-
Hiroi, K.; Suzuki, Y.; Abe, I.; Kawagishi, R. Tetrahedron 2000, 56, 4701-4710.
-
(2000)
Tetrahedron
, vol.56
, pp. 4701-4710
-
-
Hiroi, K.1
Suzuki, Y.2
Abe, I.3
Kawagishi, R.4
-
22
-
-
0035935161
-
-
(j) Hiroi, K.; Wantanabe, K.; Abe, I.; Koseki, M. Tetrahedron Lett. 2001, 42, 7617-7619.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 7617-7619
-
-
Hiroi, K.1
Wantanabe, K.2
Abe, I.3
Koseki, M.4
-
23
-
-
0037154830
-
-
(k) Priego, J.; Mancheño, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346-1353.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1346-1353
-
-
Priego, J.1
Mancheño, O.G.2
Cabrera, S.3
Carretero, J.C.4
-
24
-
-
0036514396
-
-
Wantanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372-379.
-
(2002)
Chem. Pharm. Bull.
, vol.50
, pp. 372-379
-
-
Wantanabe, K.1
Hirasawa, T.2
Hiroi, K.3
-
26
-
-
0041817833
-
-
(n) Ekegren, J. K.; Roth, P.; Källström, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358-366.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 358-366
-
-
Ekegren, J.K.1
Roth, P.2
Källström, K.3
Tarnai, T.4
Andersson, P.G.5
-
27
-
-
1042286372
-
-
(o) Hiroi, K.; Izawa, I.; Takizawa, T.; Kawai, K. Tetrahedron 2004, 60, 2155-2162.
-
(2004)
Tetrahedron
, vol.60
, pp. 2155-2162
-
-
Hiroi, K.1
Izawa, I.2
Takizawa, T.3
Kawai, K.4
-
29
-
-
0002631527
-
-
Select sulfoxides have been employed as phase-transfer catalysts. See: (a) Mikolajczyk, M.; Grzejszczak, S.; Zatorski, A.; Montanari, F.; Cinquini, M. Tetrahedron Lett. 1975, 16, 3757-3760.
-
(1975)
Tetrahedron Lett.
, vol.16
, pp. 3757-3760
-
-
Mikolajczyk, M.1
Grzejszczak, S.2
Zatorski, A.3
Montanari, F.4
Cinquini, M.5
-
30
-
-
0346350354
-
-
(b) Furukawa, N.; Kishimoto, K.; Ogawa, S.; Kawai, T.; Fujihara, H.; Oae, S. Tetrahedron Lett. 1981, 22, 4409-4412.
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 4409-4412
-
-
Furukawa, N.1
Kishimoto, K.2
Ogawa, S.3
Kawai, T.4
Fujihara, H.5
Oae, S.6
-
31
-
-
0037871675
-
-
For the use of excess chiral sulfoxide for asymmetric allylation of hydrazones and aldehydes through coordinative acceleration see: (a) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610-6611.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 6610-6611
-
-
Kobayashi, S.1
Ogawa, C.2
Konishi, H.3
Sugiura, M.4
-
32
-
-
0041508449
-
-
(b) Massa, A.; Molkov, A. V.; Kočovský, P.; Scettri, A. Tetrahedron Lett. 2003, 44, 7179-7181
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 7179-7181
-
-
Massa, A.1
Molkov, A.V.2
Kočovský, P.3
Scettri, A.4
-
33
-
-
0242541923
-
-
correction
-
(correction: Tetrahedron Lett. 2003, 44, 9067).
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 9067
-
-
-
35
-
-
0347419517
-
-
Boebel, T. A.; Gin, D. Y. Angew. Chem., Int. Ed. 2003, 42, 5874-5877.
-
(2003)
Y. Angew. Chem., Int. Ed.
, vol.42
, pp. 5874-5877
-
-
Boebel, T.A.1
Gin, D.2
-
39
-
-
32744473305
-
-
note
-
18O-incorp) to 2,3,4,6-tetra-O-methyl-D-mannopyranose.
-
-
-
-
40
-
-
32744454480
-
-
note
-
1H NMR.
-
-
-
-
41
-
-
32744477073
-
-
note
-
18O-wash-out can arise as a consequence of 1,1′-α,α′-linked disaccharide (4) formation, which provides for an even greater excess of unconsumed sulfonic anhydride at the conclusion of the process.
-
-
-
-
42
-
-
32744465610
-
-
note
-
18O-incorporation.
-
-
-
-
43
-
-
0033306129
-
-
18O-incorporation into 11 as a function of its formation. See: Rishavy, M. A.; Cleland, W. W. Can. J. Chem. 1999, 77, 967-977.
-
(1999)
Can. J. Chem.
, vol.77
, pp. 967-977
-
-
Rishavy, M.A.1
Cleland, W.W.2
-
44
-
-
0001396185
-
-
See, inter alia: (a) Jameson, C. J. J. Chem. Phys. 1977, 66, 4983-4988.
-
(1977)
J. Chem. Phys.
, vol.66
, pp. 4983-4988
-
-
Jameson, C.J.1
-
49
-
-
0003089967
-
-
Gunther, H., Ed.; Springer-Verlag: Berlin, Germany
-
(f) Risley, J. M.; Van Etten, R. L. In NMR: Basic Principles and Progress; Gunther, H., Ed.; Springer-Verlag: Berlin, Germany, 1990; Vol. 22, pp 81-168.
-
(1990)
NMR: Basic Principles and Progress
, vol.22
, pp. 81-168
-
-
Risley, J.M.1
Van Etten, R.L.2
-
50
-
-
11744314579
-
-
13C NMR has been used to study the mechanism of sulfonate exchange. See: (a) Fujio, M.; Sanematsu, F.; Tsuno, Y.; Sawada, M.; Takai, Y. Tetrahedron Lett. 1988, 29, 93-96.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 93-96
-
-
Fujio, M.1
Sanematsu, F.2
Tsuno, Y.3
Sawada, M.4
Takai, Y.5
-
51
-
-
0028929062
-
-
(b) Tsuji, Y.; Kim, S. H.; Saeki, Y.; Yatsugi, K.; Fujio, M.; Tsuno, Y. Tetrahedron Lett. 1995, 36, 1465-1468.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 1465-1468
-
-
Tsuji, Y.1
Kim, S.H.2
Saeki, Y.3
Yatsugi, K.4
Fujio, M.5
Tsuno, Y.6
-
52
-
-
6444238093
-
-
(c) Tsuji, Y.; Toteva, M. M.; Amyes, T. L.; Richard, J. P. Org. Lett. 2004, 6, 3633-3636.
-
(2004)
Org. Lett.
, vol.6
, pp. 3633-3636
-
-
Tsuji, Y.1
Toteva, M.M.2
Amyes, T.L.3
Richard, J.P.4
-
53
-
-
0005504522
-
-
This method has also been used to monitor positional isotope exchange in carbohydrates. See: (a) Mega, T. L.; Cortes, S.; Van Etten, R. L. J. Org. Chem. 1990, 55, 522-528.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 522-528
-
-
Mega, T.L.1
Cortes, S.2
Van Etten, R.L.3
-
54
-
-
0033612742
-
-
(b) Barlow, J. N.; Girvin, M. E.; Blanchard, J. S. J. Am. Chem. Soc. 1999, 121, 6968-6969.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 6968-6969
-
-
Barlow, J.N.1
Girvin, M.E.2
Blanchard, J.S.3
-
55
-
-
0142245577
-
-
Callam, C. S.; Gadikota, R. R.; Krein, D. M.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 13112-13119.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 13112-13119
-
-
Callam, C.S.1
Gadikota, R.R.2
Krein, D.M.3
Lowary, T.L.4
-
56
-
-
0002631324
-
-
Prepared from the treatment of 2,3,4,6-tetra-O-methyl-D-mannopyranose with excess hydrogen fluoride-pyridine complex, following a known procedure for the conversion of glycosyl hemiacetals to glycosyl fluorides. See: Szarek, W. A.; Grynkiewicz, G.; Doboszewski, B.; Hay, G. W. Chem. Lett. 1984, 1751-1754.
-
(1984)
Chem. Lett.
, pp. 1751-1754
-
-
Szarek, W.A.1
Grynkiewicz, G.2
Doboszewski, B.3
Hay, G.W.4
-
57
-
-
84985294852
-
-
Prepared from the treatment of benzene with trimethylsilyl chlorosulfonate following a known procedure. See: Hofman, K.; Simchen, G. Liebigs Ann. Chem. 1982, 282-297.
-
(1982)
Liebigs Ann. Chem.
, pp. 282-297
-
-
Hofman, K.1
Simchen, G.2
-
58
-
-
0003409301
-
Introduction, theory and methods
-
John Wiley & Sons: New York
-
13C-relaxation mechanisms, see: Levy, G. C.; Lichter, R. L.; Nelson, G. L. Introduction, Theory and Methods. In Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd ed.; John Wiley & Sons: New York, 1980; pp 1-28.
-
(1980)
Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd Ed.
, pp. 1-28
-
-
Levy, G.C.1
Lichter, R.L.2
Nelson, G.L.3
-
60
-
-
18944394167
-
-
18O resonances was achieved by the application of a resolution enhancement of -0.8 Hz and a Gaussian apodization of 0.5 s. The application of resolution enhancement in FT NMR has been shown to have only a limited effect on the accuracy of integration. See: Kupka, T.; Dziegielewski, J. O. Magn. Reson. Chem. 1988, 26, 353-357.
-
(1988)
Magn. Reson. Chem.
, vol.26
, pp. 353-357
-
-
Kupka, T.1
Dziegielewski, J.O.2
-
61
-
-
32744456081
-
-
[13C1-18O] (Scheme 11) would also generate pyridinium sulfonate as a byproduct.
-
[13C1-18O] (Scheme 11) would also generate pyridinium sulfonate as a byproduct.
-
-
-
-
62
-
-
32744464137
-
-
note
-
It should be noted that the advent of turnover in sulfoxide during the reaction precludes complete exclusion of the S(V7)-addition pathway (Scheme 3) from these data alone.
-
-
-
-
64
-
-
32744463745
-
-
18O-incorporation was determined by using field ionization mass spectrometry.
-
18O-incorporation was determined by using field ionization mass spectrometry.
-
-
-
-
65
-
-
32744454859
-
-
note
-
1H NMR spectra were acquired at a rate of one spectrum every 10s.
-
-
-
-
66
-
-
32744455945
-
-
note
-
2.
-
-
-
-
67
-
-
32744472159
-
-
note
-
H1 5.14 ppm, formed slowly over the course of the reaction to the extent of 2%, was determined to be 1,1′-α,α-linked disaccharide 4 (Scheme 1).
-
-
-
-
68
-
-
32744473543
-
-
note
-
The minor transient resonance at δ 5.40 may correspond to the anomeric proton of the β-anomer of mannosyl sulfonate 11, although its rigorous structural verification has yet to be achieved.
-
-
-
-
69
-
-
32744462344
-
-
note
-
1H NMR showed no change in the anomeric ratio of 9, indicating that the glycoside product did not equilibrate under the reaction conditions and that the observed 1:1 α:β mixture of glycosidic products in the glycosylation of 2-propanol to mannose hemiacetal 3 was under kinetic control.
-
-
-
-
70
-
-
0042734679
-
-
The intermediacy of an oxocarbenium species is consistent with previous observations. See: (a) Stubbs, J. M.; Marx, D. J. Am. Chem. Soc. 2003, 125, 10960-10962.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10960-10962
-
-
Stubbs, J.M.1
Marx, D.2
-
71
-
-
0037118885
-
-
(b) Abdel-Rahman, A. A.-H.; Jonke, S.; El Ashry, E. S. H.; Schmidt, R. R. Angew. Chem., Int. Ed, 2002, 41, 2972-2974.
-
(2002)
Angew. Chem., Int. Ed
, vol.41
, pp. 2972-2974
-
-
Abdel-Rahman, A.A.-H.1
Jonke, S.2
El Ashry, E.S.H.3
Schmidt, R.R.4
-
72
-
-
7244245511
-
-
(c) Crich, D.; Chandrasekera, N. S. Angew. Chem., Int. Ed. 2004, 43, 5386-5389.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 5386-5389
-
-
Crich, D.1
Chandrasekera, N.S.2
-
73
-
-
0039226889
-
-
Cook, P. F., Ed.; CRC Press: Ann Arbor, MI
-
For kinetic isotope effects associated with glycosidic bond formation/hydrolysis, see: Schramm, V. L. In Enzyme Mechanism from Isotope Effects; Cook, P. F., Ed.; CRC Press: Ann Arbor, MI, 1991; pp 367-388.
-
(1991)
Enzyme Mechanism from Isotope Effects
, pp. 367-388
-
-
Schramm, V.L.1
-
75
-
-
1642302768
-
-
(c) Lee, J. K.; Bain, A. D.; Berti, P. J. J. Am. Chem. Soc. 2004, 126, 3769-3776.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3769-3776
-
-
Lee, J.K.1
Bain, A.D.2
Berti, P.J.3
|