-
1
-
-
0032542115
-
-
For selected, recent reviews on solid phase organic synthesis see: (a) S. Booth, P. H. H. Hermkens, H. C. J. Ottenheijm and D. C. Rees, Tetrahedron, 1998, 54, 15385;
-
(1998)
Tetrahedron
, vol.54
, pp. 15385
-
-
Booth, S.1
Hermkens, P.H.H.2
Ottenheijm, H.C.J.3
Rees, D.C.4
-
6
-
-
0033574590
-
-
For reviews on linkers and cleavage strategies for solid phase organic synthesis, see: (a) I. W. James, Tetrahedron, 1999, 55, 4855;
-
(1999)
Tetrahedron
, vol.55
, pp. 4855
-
-
James, I.W.1
-
7
-
-
0033683359
-
-
(b) F. Guillier, D. Grain and M. Bradley, Chem. Rev., 2000, 100, 2091;
-
(2000)
Chem. Rev.
, vol.100
, pp. 2091
-
-
Guillier, F.1
Grain, D.2
Bradley, M.3
-
9
-
-
0035857545
-
-
(d) A. C. Comely and S. E. Gibson (née Thomas), Angew. Chem., Int. Ed., 2001, 40, 1012.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 1012
-
-
Comely, A.C.1
Gibson, S.E.2
-
10
-
-
0038145590
-
-
(a) P. C. Hutchison, T. D. Heightman and D. J. Procter, Org. Lett., 2002, 4, 4583;
-
(2002)
Org. Lett.
, vol.4
, pp. 4583
-
-
Hutchison, P.C.1
Heightman, T.D.2
Procter, D.J.3
-
11
-
-
0842264144
-
-
(b) P. C. Hutchison, T. D. Heightman and D. J. Procter, J. Org. Chem., 2004, 69, 790;
-
(2004)
J. Org. Chem.
, vol.69
, pp. 790
-
-
Hutchison, P.C.1
Heightman, T.D.2
Procter, D.J.3
-
12
-
-
0038717199
-
-
(c) N. J. Kerrigan, P. C. Hutchison, T. D. Heightman and D. J. Procter, Chem. Commun., 2003, 1402;
-
(2003)
Chem. Commun.
, pp. 1402
-
-
Kerrigan, N.J.1
Hutchison, P.C.2
Heightman, T.D.3
Procter, D.J.4
-
13
-
-
4744346554
-
-
(d) N. J. Kerrigan, P. C. Hutchison, T. D. Heightman and D. J. Procter, Org. Biomol. Chem., 2004, 2476.
-
(2004)
Org. Biomol. Chem.
, pp. 2476
-
-
Kerrigan, N.J.1
Hutchison, P.C.2
Heightman, T.D.3
Procter, D.J.4
-
14
-
-
2142715741
-
-
For recent reviews on the use of samarium(II) iodide in organic synthesis: (a) G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307;
-
(1996)
Chem. Rev.
, vol.96
, pp. 307
-
-
Molander, G.A.1
Harris, C.R.2
-
18
-
-
3543057490
-
-
(e) D. J. Edmonds, D. Johnston and D. J. Procter, Chem. Rev., 2004, 104, 3371.
-
(2004)
Chem. Rev.
, vol.104
, pp. 3371
-
-
Edmonds, D.J.1
Johnston, D.2
Procter, D.J.3
-
21
-
-
0000272655
-
-
(c) K. Otsubo, J. Inanaga and M. Yamaguchi, Tetrahedron Lett., 1987, 28, 4437;
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 4437
-
-
Otsubo, K.1
Inanaga, J.2
Yamaguchi, M.3
-
22
-
-
0000856232
-
-
(d) K. Kusuda, J. Inanaga and M. Yamaguchi, Tetrahedron Lett., 1989, 30, 2945.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 2945
-
-
Kusuda, K.1
Inanaga, J.2
Yamaguchi, M.3
-
23
-
-
0001450966
-
-
A. D. Hughes, D. A. Price and N. S. Simpkins, J. Chem. Soc., Perkin Trans. 1, 1999, 1295.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 1295
-
-
Hughes, A.D.1
Price, D.A.2
Simpkins, N.S.3
-
24
-
-
0028353822
-
-
For selected, recent examples of this reaction, see: (a) J. Castro, A. Moyano, M. A. Pericàs, A. Riera and A. E. Greene, Tetrahedron: Asymmetry, 1994, 5, 307;
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 307
-
-
Castro, J.1
Moyano, A.2
Pericàs, M.A.3
Riera, A.4
Greene, A.E.5
-
27
-
-
0035929462
-
-
(d) I. Marchueta, E. Montenegro, D. Panov, M. Poch, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, J. Org. Chem., 2001, 66, 6400.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 6400
-
-
Marchueta, I.1
Montenegro, E.2
Panov, D.3
Poch, M.4
Verdaguer, X.5
Moyano, A.6
Pericàs, M.A.7
Riera, A.8
-
28
-
-
0028604352
-
-
For selected, recent examples in the context of natural product synthesis, see: (a) I. Paterson, R. D. Norcross, R. A. Ward, P. Romea and M. A. Lister, J. Am. Chem. Soc., 1994, 116, 11287;
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 11287
-
-
Paterson, I.1
Norcross, R.D.2
Ward, R.A.3
Romea, P.4
Lister, M.A.5
-
29
-
-
0028279977
-
-
(b) R. A. Holton, C. Somoza and K.-B. Chai, Tetrahedron Lett., 1994, 35, 1665;
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 1665
-
-
Holton, R.A.1
Somoza, C.2
Chai, K.-B.3
-
32
-
-
0034827806
-
-
(e) A. D. Lebsack, L. E. Overman and R. J. Valentekovich, J. Am. Chem. Soc., 2001, 123, 4851.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 4851
-
-
Lebsack, A.D.1
Overman, L.E.2
Valentekovich, R.J.3
-
33
-
-
0040184024
-
-
(a) J. M. Concellón, J. A. Pérez-Andres and H. Rodríguez-Solla, Angew. Chem., Int. Ed., 2000, 39, 2773;
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2773
-
-
Concellón, J.M.1
Pérez-Andres, J.A.2
Rodríguez-Solla, H.3
-
34
-
-
0035886894
-
-
(b) J. M. Concellón, P. L. Bernad and H. Rodríguez-Solla, Angew. Chem., Int. Ed., 2001, 40, 3897;
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 3897
-
-
Concellón, J.M.1
Bernad, P.L.2
Rodríguez-Solla, H.3
-
35
-
-
0035898426
-
-
(c) J. M. Concellón, J. A. Pérez-Andrés and H. Rodríguez-Solla, Chem. Eur. J., 2001, 7, 3062;
-
(2001)
Chem. Eur. J.
, vol.7
, pp. 3062
-
-
Concellón, J.M.1
Pérez-Andrés, J.A.2
Rodríguez-Solla, H.3
-
38
-
-
0030901984
-
-
(a) Y. Nakamura, S. Takeuchi, Y. Ohgo, M. Yamaoka, A. Yoshida and K. Mikami, Tetrahedron Lett., 1997, 38, 2709;
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 2709
-
-
Nakamura, Y.1
Takeuchi, S.2
Ohgo, Y.3
Yamaoka, M.4
Yoshida, A.5
Mikami, K.6
-
40
-
-
0033538074
-
-
(c) Y. Nakamura, S. Takeuchi, Y. Ohgo, M. Yamaoka, A. Yoshida and K. Mikami, Tetrahedron, 1999, 55, 4595.
-
(1999)
Tetrahedron
, vol.55
, pp. 4595
-
-
Nakamura, Y.1
Takeuchi, S.2
Ohgo, Y.3
Yamaoka, M.4
Yoshida, A.5
Mikami, K.6
-
41
-
-
0031562032
-
-
Janda has reported a single, sulfone example of this linkage as a member of a different, general class of sulfone linker. Cleavage of the linker is achieved using sodium/mercury amalgam: X. Zhao, K. W. Jung and K. D. Janda, Tetrahedron Lett., 1997, 38, 977.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 977
-
-
Zhao, X.1
Jung, K.W.2
Janda, K.D.3
-
43
-
-
0141790801
-
-
We have recently developed a sulfur version of the linkage for use in solid and fluorous phase synthesis, see: (a) L. A. McAllister, S. Brand, R. de Gentile and D. J. Procter, Chem. Commun., 2003, 2380;
-
(2003)
Chem. Commun.
, pp. 2380
-
-
McAllister, L.A.1
Brand, S.2
De Gentile, R.3
Procter, D.J.4
-
44
-
-
12344302489
-
-
(b) L. A. McAllister, R. A. McCormick, S. Brand and D. J. Procter, Angew. Chem., Int. Ed., 2005, 44, 452.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 452
-
-
McAllister, L.A.1
McCormick, R.A.2
Brand, S.3
Procter, D.J.4
-
46
-
-
0032537215
-
-
(b) X. Du and R. W. Armstrong, Tetrahedron Lett., 1998, 39, 2281. Further applications of the reagent on solid phase have since been reported.;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2281
-
-
Du, X.1
Armstrong, R.W.2
-
47
-
-
0000966664
-
-
(c) R. M. Myers, S. P. Langston, S. P. Conway and C. Abell, Org. Lett., 2000, 2, 1349;
-
(2000)
Org. Lett.
, vol.2
, pp. 1349
-
-
Myers, R.M.1
Langston, S.P.2
Conway, S.P.3
Abell, C.4
-
49
-
-
0035180617
-
-
(e) M. Gustafsson, R. Olsson and C.-M. Andersson, Tetrahedron Lett., 2001, 42, 133;
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 133
-
-
Gustafsson, M.1
Olsson, R.2
Andersson, C.-M.3
-
50
-
-
0037183604
-
-
(f) M. Tanaka, A. Sudo, F. Sanda and T. Endo, Macromolecules, 2002, 35, 6845;
-
(2002)
Macromolecules
, vol.35
, pp. 6845
-
-
Tanaka, M.1
Sudo, A.2
Sanda, F.3
Endo, T.4
-
52
-
-
4644319583
-
-
See also refs 3c,3d and 12a
-
(h) S. N. Baytas, Q. Wang, N. A. Karst, J. S. Dordick and R. J. Linhardt, J. Org. Chem., 2004, 69, 6900. See also refs 3c,3d and 12a.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6900
-
-
Baytas, S.N.1
Wang, Q.2
Karst, N.A.3
Dordick, J.S.4
Linhardt, R.J.5
-
53
-
-
0034674964
-
-
R. S. Miller, J. M. Sealy, M. Shabangi, M. L. Kuhlman, J. R. Fuchs and R. A. Flowers II, J. Am. Chem. Soc., 2000, 122, 7718.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 7718
-
-
Miller, R.S.1
Sealy, J.M.2
Shabangi, M.3
Kuhlman, M.L.4
Fuchs, J.R.5
Flowers II, R.A.6
-
54
-
-
0002468910
-
-
ed. S. Kobayashi, Springer, New York
-
2 reactions, see: H. Kagan and J. L. Namy in Lanthanides: Chemistry and Use in Organic Synthesis; ed. S. Kobayashi, Springer, New York, 1999, p. 155.
-
(1999)
Lanthanides: Chemistry and Use in Organic Synthesis
, pp. 155
-
-
Kagan, H.1
Namy, J.L.2
-
56
-
-
0037165747
-
-
-1. J. P. Stevenson, W. F. Jackson and J. M. Tanko, J. Am. Chem. Soc., 2002, 124, 4271.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4271
-
-
Stevenson, J.P.1
Jackson, W.F.2
Tanko, J.M.3
-
57
-
-
0026059141
-
-
The fragmentation of cyclopropyl ketones on treatment with samarium(II) iodide has been exploited previously in both synthetic and mechanistic contexts. (a) R. A. Batey and W. B. Motherwell, Tetrahedron Lett., 1991, 43, 6211;
-
(1991)
Tetrahedron Lett.
, vol.43
, pp. 6211
-
-
Batey, R.A.1
Motherwell, W.B.2
-
59
-
-
0030962154
-
-
(c) D. P. Curran, X. Gu, W. Zhang and P. Dowd, Tetrahedron, 1997, 53, 9023;
-
(1997)
Tetrahedron
, vol.53
, pp. 9023
-
-
Curran, D.P.1
Gu, X.2
Zhang, W.3
Dowd, P.4
-
60
-
-
0036263466
-
-
(d) G. Masson, S. Py and Y. Vallée, Angew. Chem., Int. Ed., 2002, 41, 1772;
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 1772
-
-
Masson, G.1
Py, S.2
Vallée, Y.3
-
61
-
-
0011960238
-
-
(e) T. K. Hutton, K. Muir and D. J. Procter, Org. Lett., 2002, 4, 2345;
-
(2002)
Org. Lett.
, vol.4
, pp. 2345
-
-
Hutton, T.K.1
Muir, K.2
Procter, D.J.3
-
62
-
-
0346422364
-
-
(f) T. K. Hutton, K. W. Muir and D. J. Procter, Org. Lett., 2003, 5, 4811.
-
(2003)
Org. Lett.
, vol.5
, pp. 4811
-
-
Hutton, T.K.1
Muir, K.W.2
Procter, D.J.3
-
63
-
-
33645271369
-
-
note
-
Molander and Inanaga have invoked the direct reduction of the α-substituent in the case of α-bromo esters (ref. 5a) and α,β-epoxy esters (ref. 5c), respectively.
-
-
-
-
66
-
-
0032543511
-
-
(c) S. Ichikawa, S. Shuto and A. Matsuda, Tetrahedron Lett., 1998, 39, 4525;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4525
-
-
Ichikawa, S.1
Shuto, S.2
Matsuda, A.3
-
68
-
-
0034598547
-
-
(a) M. Ricci, L. Madariaga and T. Skrydstrup, Angew. Chem., Int. Ed., 2000, 39, 242;
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 242
-
-
Ricci, M.1
Madariaga, L.2
Skrydstrup, T.3
-
69
-
-
0034694729
-
-
(b) M. Ricci, P. Blakskjær and T. Skrydstrup, J. Am. Chem. Soc., 2000, 122, 12413.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 12413
-
-
Ricci, M.1
Blakskjær, P.2
Skrydstrup, T.3
-
70
-
-
33645273922
-
-
note
-
Adduct 26 could conceivably be formed by radical addition to methylacrylate. The analogous reaction using an electronically matched radical acceptor, ethyl vinyl ether gave no addition products suggesting 26 is formed by an anionic process.
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