-
6
-
-
0035351150
-
-
J. A. Tallarico, K. M. Depew, H. E. Pelish, N. J. Westwood, C. W. Lindsley, M. D. Shair, S. L. Schreiber, M. A. Foley, J. Comb. Chem. 2001, 3, 312.
-
(2001)
J. Comb. Chem.
, vol.3
, pp. 312
-
-
Tallarico, J.A.1
Depew, K.M.2
Pelish, H.E.3
Westwood, N.J.4
Lindsley, C.W.5
Shair, M.D.6
Schreiber, S.L.7
Foley, M.A.8
-
7
-
-
0035542849
-
-
a) H. E. Blackwell, L. Pérez, R. A. Stavenger, J. A. Tallarico, E. Cope Etough, M. A. Foley, S. L. Schreiber, Chem. Biol. 2001. 8, 1167;
-
(2001)
Chem. Biol.
, vol.8
, pp. 1167
-
-
Blackwell, H.E.1
Pérez, L.2
Stavenger, R.A.3
Tallarico, J.A.4
Cope Etough, E.5
Foley, M.A.6
Schreiber, S.L.7
-
8
-
-
0035542853
-
-
b) P. A. Clemons, A. N. Koehler, B. K. Wagner, T. G. Sprigings, D. R. Spring, R. W. King, S. L. Schreiber, Chem. Biol. 2001, 8, 1183.
-
(2001)
Chem. Biol.
, vol.8
, pp. 1183
-
-
Clemons, P.A.1
Koehler, A.N.2
Wagner, B.K.3
Sprigings, T.G.4
Spring, D.R.5
King, R.W.6
Schreiber, S.L.7
-
11
-
-
0033598258
-
-
M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs. Org. Lett. 1999, 1, 953.
-
(1999)
Org. Lett.
, vol.1
, pp. 953
-
-
Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
-
12
-
-
0000826186
-
-
a) R. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem. 1995, 707, 2179;
-
(1995)
Angew. Chem.
, vol.707
, pp. 2179
-
-
Schwab, R.1
France, M.B.2
Ziller, J.W.3
Grubbs, R.H.4
-
14
-
-
0001855961
-
-
b) R. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100;
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 100
-
-
Schwab, R.1
Grubbs, R.H.2
Ziller, J.W.3
-
18
-
-
0034734340
-
-
S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 722, 8168.
-
(2000)
J. Am. Chem. Soc.
, vol.722
, pp. 8168
-
-
Garber, S.B.1
Kingsbury, J.S.2
Gray, B.L.3
Hoveyda, A.H.4
-
19
-
-
0003008165
-
-
For examples of the effects of changing linker length and constitution on reaction outcome in 1% DVB polystyrene, see: a) B. Yan, Q. Sun, J. Org. Chem. 1998, 63, 55;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 55
-
-
Yan, B.1
Sun, Q.2
-
20
-
-
0033958525
-
-
b) C. W. Lindsley, L. K. Chan, B. C. Goess, R. Joseph, M. D. Shair, J. Am. Chem. Soc. 2000, 722, 422.
-
(2000)
J. Am. Chem. Soc.
, vol.722
, pp. 422
-
-
Lindsley, C.W.1
Chan, L.K.2
Goess, B.C.3
Joseph, R.4
Shair, M.D.5
-
22
-
-
0012748919
-
-
For possible effects of propargyl heteroatom substitution on enyne metathesis reactions, see: S. Randl, N. Lucas, S. J. Connon, S. Blechert, Adv. Synth. Catal. 2002, 344, 631.
-
(2002)
Adv. Synth. Catal.
, vol.344
, pp. 631
-
-
Randl, S.1
Lucas, N.2
Connon, S.J.3
Blechert, S.4
-
23
-
-
24344444420
-
-
note
-
Initial intermolecular enyne metathesis, involving equilibration to a double-bond geometry that permits formation of a potentially thermodynamically more stable product containing a six-membered cyclic boronic ester, has not been ruled out. However, the failure to generate more than trace amounts of the desired cyclic dialkenylboronic ester when the pinacol alkynylboronic ester was used in place of the diisopropyl boronic ester in a solution phase enyne metathesis reaction suggests that this pathway is less significant.
-
-
-
-
26
-
-
0033614857
-
-
b) T. R. Hoye, S. M. Donaldson, T. J. Vos, Org. Lett. 1999, 1, 277.
-
(1999)
Org. Lett.
, vol.1
, pp. 277
-
-
Hoye, T.R.1
Donaldson, S.M.2
Vos, T.J.3
-
28
-
-
24344484690
-
-
(Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim
-
For recent descriptions of solid phase olefin metathesis, see: a) F. Zaragoza in Handbook of Combinatorial Chemistry. Vol. 1 (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, p. 595;
-
(2002)
Handbook of Combinatorial Chemistry
, vol.1
, pp. 595
-
-
Zaragoza, F.1
-
30
-
-
0029860486
-
-
For examples requiring higher pre-catalyst loadings, see: a) S. J. Miller, H. E. Blackwell, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 9606;
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9606
-
-
Miller, S.J.1
Blackwell, H.E.2
Grubbs, R.H.3
-
34
-
-
0037037836
-
-
e) S. Chang, Y. Na, H. J. Shin, E. Choi, L. S. Jeong, Tetrahedron Lett. 2002, 43, 7445;
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 7445
-
-
Chang, S.1
Na, Y.2
Shin, H.J.3
Choi, E.4
Jeong, L.S.5
-
35
-
-
0037073163
-
-
f) B. A. Harrison, T. M. Gierasch, C. Neilan, G. W. Pasternak, G. L. Verdine, J. Am. Chem. Soc. 2002. 124, 13352;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13352
-
-
Harrison, B.A.1
Gierasch, T.M.2
Neilan, C.3
Pasternak, G.W.4
Verdine, G.L.5
-
36
-
-
0942289842
-
-
g) P. Arya, P. Durieux, Z. X. Chen, R. Joseph, D.M. Leek, J. Comb. Chem. 2004, 6, 54. For examples requiring changes in linker/resin, see:
-
(2004)
J. Comb. Chem.
, vol.6
, pp. 54
-
-
Arya, P.1
Durieux, P.2
Chen, Z.X.3
Joseph, R.4
Leek, D.M.5
-
38
-
-
0037032265
-
-
i) D. Brohm, N. Philippe, S. Metzger, A. Bhargava, O. Muller, F. Lieb, H. Waldmann, J. Am. Chem. Soc. 2002, 124, 13171;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13171
-
-
Brohm, D.1
Philippe, N.2
Metzger, S.3
Bhargava, A.4
Muller, O.5
Lieb, F.6
Waldmann, H.7
-
39
-
-
1842586978
-
-
j) J.-D. Moriggi, L. J. Brown, J. L. Castro, R. C. D. Brown, Org. Biomol. Chem. 2004, 2, 835;
-
(2004)
Org. Biomol. Chem.
, vol.2
, pp. 835
-
-
Moriggi, J.-D.1
Brown, L.J.2
Castro, J.L.3
Brown, R.C.D.4
-
40
-
-
2942516854
-
-
k) V. Chaleix, V. Sol, M. Guilloton, R. Granet, P. Krausz, Tetrahedron Lett. 2004. 45, 5295.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 5295
-
-
Chaleix, V.1
Sol, V.2
Guilloton, M.3
Granet, R.4
Krausz, P.5
-
41
-
-
0030569374
-
-
For examples requiring additives, see: l) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse. Tetrahedron Lett. 1996, 37, 8249;
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 8249
-
-
Van Maarseveen, J.H.1
Den Hartog, J.A.J.2
Engelen, V.3
Finner, E.4
Visser, G.5
Kruse, C.G.6
-
42
-
-
2842617271
-
-
m) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra, F. P. T. J. Rutjes, Enr. J. Org. Chem. 1998, 2583:
-
(1998)
Enr. J. Org. Chem.
, pp. 2583
-
-
Veerman, J.J.N.1
Van Maarseveen, J.H.2
Visser, G.M.3
Kruse, C.G.4
Schoemaker, H.E.5
Hiemstra, H.6
Rutjes, F.P.T.J.7
-
43
-
-
0034613125
-
-
n) S. Varray, C. Gauzy, F. Lamaty, R. Lazaro, J. Martinez, J. Org. Chem. 2000. 65, 6787;
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6787
-
-
Varray, S.1
Gauzy, C.2
Lamaty, F.3
Lazaro, R.4
Martinez, J.5
-
45
-
-
33644994354
-
-
A high degree of site separation exists in regular 1% DVB cross-linked polystyrene resins but, due to the dynamic nature of the matrix, at least some amount of transient site interaction always occurs, see ref. [11a]. For an early account of site-site interactions, sec: H. Rapoport, J. I. Crowley. Acc. Chem. Res. 1976, 9, 135.
-
(1976)
Acc. Chem. Res.
, vol.9
, pp. 135
-
-
Rapoport, H.1
Crowley, J.I.2
-
46
-
-
24344491112
-
-
note
-
Although the homoallylic alcohols are all part of the same polymeric molecule, reaction with another support-bound substrate will still be referred to as intermolecular.
-
-
-
-
50
-
-
0042390682
-
-
c) H-Y. Lee, B. G. Kim, M. L. Snapper, Org. Lett. 2003, 5, 1855.
-
(2003)
Org. Lett.
, vol.5
, pp. 1855
-
-
Lee, H.-Y.1
Kim, B.G.2
Snapper, M.L.3
-
51
-
-
0038296931
-
-
For recent examples, see: a) M. Mori, N. Saito, D. Tanaka, M. Takimoto, Y. Sato, J. Am. Chem. Soc. 2003, 125, 5606;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 5606
-
-
Mori, M.1
Saito, N.2
Tanaka, D.3
Takimoto, M.4
Sato, Y.5
-
52
-
-
1242307394
-
-
b) A. G. M. Barrett, A. J. Hennessy, R. Le Vezouet, P. A. Procopiou, P. W. Scale, S. Stefaniak, R. J. Upton, A. J. P. White, D. J. Williams, J. Org. Chem. 2004, 69, 1028.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 1028
-
-
Barrett, A.G.M.1
Hennessy, A.J.2
Le Vezouet, R.3
Procopiou, P.A.4
Scale, P.W.5
Stefaniak, S.6
Upton, R.J.7
White, A.J.P.8
Williams, D.J.9
-
53
-
-
24344499520
-
-
note
-
1H MAS-NMR.
-
-
-
-
54
-
-
0037716294
-
-
Various copper salts have also been shown to aid metathesis reactions, (see: M. Rivard, S. Blechert, Eur. J. Org. Chem. 2003, 2225) but these offered no significant improvements in this case.
-
(2003)
Eur. J. Org. Chem.
, pp. 2225
-
-
Rivard, M.1
Blechert, S.2
-
55
-
-
0043194171
-
-
A. K. Chatterjee, T.-L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 725, 11360.
-
(2003)
J. Am. Chem. Soc.
, vol.725
, pp. 11360
-
-
Chatterjee, A.K.1
Choi, T.-L.2
Sanders, D.P.3
Grubbs, R.H.4
-
56
-
-
24344498262
-
-
note
-
It may be hypothesized that under these conditions, a propagating carbene would be very similar to that generated when catalyst 3 is used as the pre-catalyst.
-
-
-
-
57
-
-
0034814443
-
-
M. S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 6543.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 6543
-
-
Sanford, M.S.1
Love, J.A.2
Grubbs, R.H.3
-
59
-
-
0035108849
-
-
b) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430;
-
(2001)
Synlett
, pp. 430
-
-
Randl, S.1
Gessler, S.2
Wakamatsu, H.3
Blechert, S.4
-
60
-
-
0034804462
-
-
c) S. Randl, N. Buschmann, S. J. Cannon, S. Blechert, Synlett 2001, 1547;
-
(2001)
Synlett
, pp. 1547
-
-
Randl, S.1
Buschmann, N.2
Cannon, S.J.3
Blechert, S.4
-
61
-
-
0038238936
-
-
d) J. A. Love, J. P. Morgan, T. M. Trnka, R. H. Grubbs, Angew. Chem. 2002, 114, 4207;
-
(2002)
Angew. Chem.
, vol.114
, pp. 4207
-
-
Love, J.A.1
Morgan, J.P.2
Trnka, T.M.3
Grubbs, R.H.4
-
63
-
-
1642462100
-
-
A. H. Hoveyda, D. G. Gillingham, J. J. van Veldhuizen, O. Kataoaka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity, Org. Biomol. Chem. 2003, 2, 8.
-
(2003)
Org. Biomol. Chem.
, vol.2
, pp. 8
-
-
Hoveyda, A.H.1
Gillingham, D.G.2
Van Veldhuizen, J.J.3
Kataoaka, O.4
Garber, S.B.5
Kingsbury, J.S.6
Harrity, J.P.A.7
-
64
-
-
24344476242
-
-
See http://www.synphase.com for details.
-
-
-
-
65
-
-
24344503714
-
-
note
-
Although substrate concentrations vary between solid and solutionphase reactions, these results show that substrate concentration is not believed to be a contributory factor in the crossover phenomenon. Additionally, running solution-phase experiments under more concentrated conditions (0.5-1 M relative to homoallylic alcohol) did not effect the trend, with catalyst 3 being superior in these cases.
-
-
-
-
66
-
-
0035912363
-
-
For examples of deliberate covalent bond formation between support-bound substrates, see: a) H. E. Blackwell, P. A. demons, S. L. Schreiber, Org. Lett. 2001, 3, 1185:
-
(2001)
Org. Lett.
, vol.3
, pp. 1185
-
-
Blackwell, H.E.1
Demons, P.A.2
Schreiber, S.L.3
-
67
-
-
0037686221
-
-
b) Y. Liao, R. Fathi, Z. Yang, J. Comb. Chem. 2003, 5, 79;
-
(2003)
J. Comb. Chem.
, vol.5
, pp. 79
-
-
Liao, Y.1
Fathi, R.2
Yang, Z.3
-
68
-
-
0037462098
-
-
c) B. Olenyuk, C. Jitianu, P. B. Dervan, J. Am. Chem. Soc. 2003, 125, 4741.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 4741
-
-
Olenyuk, B.1
Jitianu, C.2
Dervan, P.B.3
-
69
-
-
24344499747
-
-
note
-
Examples of metathesis reactions in which facilitating the release of ruthenium may prove helpful include: enyne metathesis, ring-opening metathesis (ROM), and tandem ring closing/ring-opening metathesis (RCM/ROM).
-
-
-
|