-
2
-
-
29444442296
-
-
For recent reviews in C-glycoside biology, see: (a) Lin, C.-H.; Lin, H.-C.; Yang, W.-B. Curr. Toy. Med. Chem. 2005, 5, 1431.
-
For recent reviews in C-glycoside biology, see: (a) Lin, C.-H.; Lin, H.-C.; Yang, W.-B. Curr. Toy. Med. Chem. 2005, 5, 1431.
-
-
-
-
9
-
-
0032552046
-
-
(c) Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913.
-
(1998)
Tetrahedron
, vol.54
, pp. 9913
-
-
Du, Y.1
Linhardt, R.J.2
Vlahov, I.R.3
-
11
-
-
0033588359
-
-
(a) Cotanda, K.; Matsugi, M.; SueMura, M.; Ohira, C.; Sano, A.; Oka, M.; Kita, Y. Tetrahedron 1999, 55, 10315.
-
(1999)
Tetrahedron
, vol.55
, pp. 10315
-
-
Cotanda, K.1
Matsugi, M.2
SueMura, M.3
Ohira, C.4
Sano, A.5
Oka, M.6
Kita, Y.7
-
12
-
-
0001351069
-
-
(b) Giese, B.; Dupuis, J.; Nix, M. Org. Synth. 1987, 65, 236.
-
(1987)
Org. Synth
, vol.65
, pp. 236
-
-
Giese, B.1
Dupuis, J.2
Nix, M.3
-
13
-
-
0001326751
-
-
(c) Dupuis, J.; Giese, B.; Hartung, J.; Leising, M.; Korth, H.-G.; Sustmann, R. J. Am. Chem. Soc. 1985, 107, 4332.
-
(1985)
J. Am. Chem. Soc
, vol.107
, pp. 4332
-
-
Dupuis, J.1
Giese, B.2
Hartung, J.3
Leising, M.4
Korth, H.-G.5
Sustmann, R.6
-
14
-
-
84985534838
-
-
(d) Giese, B.; Dupuis, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 622.
-
(1983)
Angew. Chem., Int. Ed. Engl
, vol.22
, pp. 622
-
-
Giese, B.1
Dupuis, J.2
-
15
-
-
37049094999
-
-
(e) Adlington, R. M.; Baldwin, J. E.; Basak, A.; Kozyrod, R. P. J. Chem. Soc. Chem. Commun. 1983, 944.
-
(1983)
J. Chem. Soc. Chem. Commun
, pp. 944
-
-
Adlington, R.M.1
Baldwin, J.E.2
Basak, A.3
Kozyrod, R.P.4
-
16
-
-
0038055611
-
-
For a leading review on transition-met al.-mediated radical reactions, see
-
For a leading review on transition-met al.-mediated radical reactions, see: Gansauer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
-
(2000)
Chem. Rev
, vol.100
, pp. 2771
-
-
Gansauer, A.1
Bluhm, H.2
-
17
-
-
0023669624
-
-
For Mn, see: a
-
For Mn, see: (a) DeShong, P.; Slough, G. A.; Elango, V. Carbohydr. Res. 1987, 171, 342.
-
(1987)
Carbohydr. Res
, vol.171
, pp. 342
-
-
DeShong, P.1
Slough, G.A.2
Elango, V.3
-
18
-
-
0037007710
-
-
For Ti, see
-
(b) For Ti, see: Parrish, J. D.; Little, R. D. Org. Lett. 2002, 4, 1439.
-
(2002)
Org. Lett
, vol.4
, pp. 1439
-
-
Parrish, J.D.1
Little, R.D.2
-
20
-
-
34548473301
-
-
For Cr, see
-
(d) For Cr, see: Juhasz, Z.; Micskei, K.; Gal, E.; Somsak, L. Tetrahedron Lett. 2007, 48, 7351.
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 7351
-
-
Juhasz, Z.1
Micskei, K.2
Gal, E.3
Somsak, L.4
-
21
-
-
0004343469
-
-
Catalytic Co/stoichiometric Zn
-
(a) Catalytic Co/stoichiometric Zn: Scheffold, R.; Abrecht, S.; Orlinski, R.; Ruf, H.-R. Pure Appl. Chem. 1987, 59, 363.
-
(1987)
Pure Appl. Chem
, vol.59
, pp. 363
-
-
Scheffold, R.1
Abrecht, S.2
Orlinski, R.3
Ruf, H.-R.4
-
22
-
-
0033693866
-
-
Catalytic Ni (II) /stoichiometric Mn: Readman, S. K.; Marsden, S. P.; Hodgson, A. Synlett., 2000, 1628.
-
(b) Catalytic Ni (II) /stoichiometric Mn: Readman, S. K.; Marsden, S. P.; Hodgson, A. Synlett., 2000, 1628.
-
-
-
-
23
-
-
37049075549
-
-
The glucosyl radical is known to adopt a boat conformation, while the mannosyl radical is a chair: (a) Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. J. Chem. Soc., Perkin Trans. 2 1986, 1453.
-
The glucosyl radical is known to adopt a boat conformation, while the mannosyl radical is a chair: (a) Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. J. Chem. Soc., Perkin Trans. 2 1986, 1453.
-
-
-
-
24
-
-
84985520838
-
-
(b) Dupuis, J.; Giese, B.; Rüegge, D.; Fishcer, H.; Korth, H.-G.; Sustmann, R. Angew. Chem., Int. Ed. Enel. 1984, 23, 896.
-
(1984)
Angew. Chem., Int. Ed. Enel
, vol.23
, pp. 896
-
-
Dupuis, J.1
Giese, B.2
Rüegge, D.3
Fishcer, H.4
Korth, H.-G.5
Sustmann, R.6
-
26
-
-
33847301925
-
-
For a related example of Ni-catalyzed C-alkylation, see: Gong, H.; Sinisi, R.; Gagné, M. R. J. Am. Chem. Soc. 2007, 129, 1908.
-
For a related example of Ni-catalyzed C-alkylation, see: Gong, H.; Sinisi, R.; Gagné, M. R. J. Am. Chem. Soc. 2007, 129, 1908.
-
-
-
-
31
-
-
36749022699
-
-
For examples of cross-coupling with a putative radical cyclization prior to C-C bond formation, see: (a) Phapale, V. B, Buñuel, E, García-Iglesias, M, Càrdenas, D. J. Angew. Chem, Int. Ed. 2007, 46, 8790
-
For examples of cross-coupling with a putative radical cyclization prior to C-C bond formation, see: (a) Phapale, V. B.; Buñuel, E.; García-Iglesias, M.; Càrdenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790.
-
-
-
-
33
-
-
12944309312
-
-
(c) Powell, D. A.; Maki, T.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 510.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 510
-
-
Powell, D.A.1
Maki, T.2
Fu, G.C.3
-
34
-
-
34447328777
-
-
For examples of SmI2-mediated C-glycoside synthesis invoking radical intermediates, see: (a) Malapelle, A, Coslovi, A, Doisneau, G, Beau, J.-M. Eur. J. Org. Chem. 2007, 3145
-
2-mediated C-glycoside synthesis invoking radical intermediates, see: (a) Malapelle, A.; Coslovi, A.; Doisneau, G.; Beau, J.-M. Eur. J. Org. Chem. 2007, 3145.
-
-
-
-
37
-
-
0030442944
-
-
(d) Hung, S.-C.; Wong, C.-H. Angew. Chem., Int. Ed. Enel. 1996, 35, 2671.
-
(1996)
Angew. Chem., Int. Ed. Enel
, vol.35
, pp. 2671
-
-
Hung, S.-C.1
Wong, C.-H.2
-
39
-
-
0034680596
-
-
For an example involving Ni cocatalysis, see
-
(f) For an example involving Ni cocatalysis, see: Miquel, N.; Doisneau, G.; Beau, J.-M. Angew. Chem., Int. Ed. 2000, 39, 4111.
-
(2000)
Angew. Chem., Int. Ed
, vol.39
, pp. 4111
-
-
Miquel, N.1
Doisneau, G.2
Beau, J.-M.3
-
40
-
-
84962339561
-
-
For mechanistic and computational studies that implicate radical intermediates in Ni-catalyzed Negishi reactions, see: (a) Lin, X, Phillips, D. L. J. Org. Chem. 2008, 73, 3680
-
For mechanistic and computational studies that implicate radical intermediates in Ni-catalyzed Negishi reactions, see: (a) Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680.
-
-
-
-
41
-
-
33749519198
-
-
(b) Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Kanovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 13175
-
-
Jones, G.D.1
Martin, J.L.2
McFarland, C.3
Allen, O.R.4
Hall, R.E.5
Haley, A.D.6
Brandon, R.J.7
Kanovalova, T.8
Desrochers, P.J.9
Pulay, P.10
Vicic, D.A.11
-
42
-
-
84869271931
-
-
2 (10 mol %), ligand (15 mol %), proton source (200 mol %), DMA (0.24 M), rt, 12 h. See the Supporting Informationfor further details.
-
2 (10 mol %), ligand (15 mol %), proton source (200 mol %), DMA (0.24 M), rt, 12 h. See the Supporting Informationfor further details.
-
-
-
-
43
-
-
64349104536
-
-
Subjection of glucal 3 to the standerd conditions in the presence of methyl acrylate resulted in no reaction.
-
Subjection of glucal 3 to the standerd conditions in the presence of methyl acrylate resulted in no reaction.
-
-
-
-
44
-
-
64349085654
-
-
The Zn-mediated reductive elimination of aceto-1-glycosyl bromides is well known from the Fischer-Zach glycal synthesis: Fischer, E.; Zach, K. Sitzungsber. Kl. Preuss. Akad. Wiss. 1913, 27, 311.
-
The Zn-mediated reductive elimination of aceto-1-glycosyl bromides is well known from the Fischer-Zach glycal synthesis: Fischer, E.; Zach, K. Sitzungsber. Kl. Preuss. Akad. Wiss. 1913, 27, 311.
-
-
-
-
45
-
-
64349097132
-
-
Attempts to suppress hydrolysis product 4 through the use of desiccants (molecular sieves, etc.) were unsuccessful.
-
Attempts to suppress hydrolysis product 4 through the use of desiccants (molecular sieves, etc.) were unsuccessful.
-
-
-
-
46
-
-
3242706187
-
-
For example, see: a
-
For example, see: (a) Liu, Y.; Gallagher, T. Org. Lett. 2004, 6, 2445.
-
(2004)
Org. Lett
, vol.6
, pp. 2445
-
-
Liu, Y.1
Gallagher, T.2
-
47
-
-
0034649720
-
-
(b) SanMartin, R.; Tavassoli, B.; Walsh, K. E.; Walter, D. S.; Gallagher, T. Org. Lett. 2000, 2, 4051.
-
(2000)
Org. Lett
, vol.2
, pp. 4051
-
-
SanMartin, R.1
Tavassoli, B.2
Walsh, K.E.3
Walter, D.S.4
Gallagher, T.5
-
48
-
-
64349088987
-
-
For examples of the known difficulty in obtaining high selectivity in reactions of arabinosyl-type radicals, see refs 1 and 6d
-
For examples of the known difficulty in obtaining high selectivity in reactions of arabinosyl-type radicals, see refs 1 and 6d.
-
-
-
-
49
-
-
64349107289
-
-
Attempts to improve yields by using the Bn-protected glucosyl or mannosyl chlorides failed no reaction
-
Attempts to improve yields by using the Bn-protected glucosyl or mannosyl chlorides failed (no reaction).
-
-
-
-
50
-
-
84869271929
-
-
1H NMR; for this reason, glucosyl bromide 27 was used thereafter.
-
1H NMR; for this reason, glucosyl bromide 27 was used thereafter.
-
-
-
-
51
-
-
64349099816
-
-
The configuration of the stereocenter a to the methyl ester in the major isomer of 29 was determined by single-crystal X-ray analysis (see the Supporting Information).
-
The configuration of the stereocenter a to the methyl ester in the major isomer of 29 was determined by single-crystal X-ray analysis (see the Supporting Information).
-
-
-
-
53
-
-
0032491776
-
-
2, rt, 48 h. See: Evans, D. A.; Coleman, P. J.; Carlos Dias, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2738.
-
2, rt, 48 h. See: Evans, D. A.; Coleman, P. J.; Carlos Dias, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2738.
-
-
-
-
54
-
-
34347257749
-
-
For recent examples of Ni-catalyzed reductive coupling reactions involving transmet al.ation with dialkylzinc species, see: a
-
For recent examples of Ni-catalyzed reductive coupling reactions involving transmet al.ation with dialkylzinc species, see: (a) Montgomery, J.; Sormunen, G. J. Top. Curr. Chem. 2007, 279, 1.
-
(2007)
Top. Curr. Chem
, vol.279
, pp. 1
-
-
Montgomery, J.1
Sormunen, G.J.2
-
55
-
-
44649187386
-
-
(b) Cozzi, P. G.; Mignogna, A.; Zoli, L. Pure Appl Chem. 2008, 80, 891.
-
(2008)
Pure Appl Chem
, vol.80
, pp. 891
-
-
Cozzi, P.G.1
Mignogna, A.2
Zoli, L.3
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