-
1
-
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0032580376
-
-
For recent reviews on ROM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
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(1998)
Tetrahedron
, vol.54
, pp. 4413-4450
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Grubbs, R.H.1
Chang, S.2
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2
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0000755941
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(b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2056.
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Angew. Chem., Int. Ed. Engl.
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, pp. 2037-2056
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Schuster, M.1
Blechert, S.2
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3
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1542763298
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Grubbs, R. H.; Miller, S. J.; Fu, G. C. Ace. Chem. Res. 1995, 28, 446-452.
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(1995)
Ace. Chem. Res.
, vol.28
, pp. 446-452
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Grubbs, R.H.1
Miller, S.J.2
Fu, G.C.3
-
4
-
-
0000652169
-
-
For examples of RCM with tungsten and molybdenum alkylidenes, see: (a) Leconte, M.; Salvatore, P.; Mutch, A.; Lefebvre, F.; Basset, J. M. Bull. Soc. Chem. Fr. 1995, 132, 1069-1071.
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(1995)
Bull. Soc. Chem. Fr.
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Leconte, M.1
Salvatore, P.2
Mutch, A.3
Lefebvre, F.4
Basset, J.M.5
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5
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0000315733
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(b) Nugent, W. A.; Feldman, J.; Calabrese, J. C. J. Am. Chem. Soc. 1995, 117, 8992-8998.
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(1995)
J. Am. Chem. Soc.
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, pp. 8992-8998
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Nugent, W.A.1
Feldman, J.2
Calabrese, J.C.3
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9
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78249281266
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Fu, G. C.; Nguyen, S. T.; Grubbs, R. H.; J. Am. Chem. Soc. 1993, 115, 9856-9857.
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(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 9856-9857
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Fu, G.C.1
Nguyen, S.T.2
Grubbs, R.H.3
-
10
-
-
0001855961
-
-
(a) Schwab, P.; Grubbs, R. H.; Ziller, J. W, J. Am. Chem. Soc. 1996, 118, 100-110.
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(1996)
J. Am. Chem. Soc.
, vol.118
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Schwab, P.1
Grubbs, R.H.2
Ziller, J.W.3
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11
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33746236970
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(b) Schwab, P.; France, M. B.; Grubbs, R. H.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
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(1995)
Angew. Chem., Int. Ed. Engl.
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Schwab, P.1
France, M.B.2
Grubbs, R.H.3
Ziller, J.W.4
-
12
-
-
0030889136
-
-
For additional examples of the functional group tolerance of 1, see (a) Meng, D.; Su, D.-S.; Balog, A.; Bertinato, P.; Sorenson, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. J. Am. Chem. Soc. 1997,119, 2733-2734.
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(1997)
J. Am. Chem. Soc.
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Meng, D.1
Su, D.-S.2
Balog, A.3
Bertinato, P.4
Sorenson, E.J.5
Danishefsky, S.J.6
Zheng, Y.-H.7
Chou, T.-C.8
He, L.9
Horwitz, S.B.10
-
13
-
-
0029860486
-
-
(b) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
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(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9606-9614
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Miller, S.J.1
Blackwell, H.E.2
Grubbs, R.H.3
-
14
-
-
33847520251
-
-
Alkylidene 1 is inactive in polar, aprotic solvents such as DMSO and DMF.
-
Alkylidene 1 is inactive in polar, aprotic solvents such as DMSO and DMF.
-
-
-
-
15
-
-
0030726065
-
-
and references therein
-
(a) Kanai, M.; Mortell, K. H.; Kiessling, L. L. J. Am. Chem. Soc. 1997, 119, 9931-9932, and references therein.
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J. Am. Chem. Soc.
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, pp. 9931-9932
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Kanai, M.1
Mortell, K.H.2
Kiessling, L.L.3
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16
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-
0001090765
-
-
(b) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784-790.
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(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 784-790
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Lynn, D.M.1
Kanaoka, S.2
Grubbs, R.H.3
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19
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0029846989
-
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(b) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
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Xu, Z.1
Johannes, C.W.2
Salman, S.S.3
Hoveyda, A.H.4
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22
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-
0001847655
-
-
For general references on solid supported ROM, see: (a) Peters, J.-U.; Blechert, S. Synlett. 1997, 348-350.
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(1997)
Synlett.
, pp. 348-350
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Peters, J.-U.1
Blechert, S.2
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24
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0030693762
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-
Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146.
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(1997)
Tetrahedron Lett.
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, pp. 7143-7146
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Piscopio, A.D.1
Miller, J.F.2
Koch, K.3
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25
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0030569374
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-
van Maarseveen, J. H.; den Hartog, J. A. J.; Engelen, V.; Finner, E.; Visser, G.; Kruse, C. G. Tetrahedron Lett. 1996, 37, 8249-8252.
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 8249-8252
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Van Maarseveen, J.H.1
Den Hartog, J.A.J.2
Engelen, V.3
Finner, E.4
Visser, G.5
Kruse, C.G.6
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26
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0029903708
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(e) Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1979-1980.
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Angew. Chem., Int. Ed. Engl.
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Schuster, M.1
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Blechert, S.3
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28
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0029975056
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For general reviews of other carbon-carbon bond forming processes in water, see: (a) Li, C. J. Tetrahedron 1996,52,5643-5668.
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(1996)
Tetrahedron
, pp. 5643-5668
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Li, C.J.1
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30
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0001740420
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(a) Hillmyer, M. A.; Lepetit, C.; McGrath, D. V.; Novak, B. M.; Grubbs, R. H. Macromolecules 1992,25, 3345-3350.
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(1992)
Macromolecules
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-
Hillmyer, M.A.1
Lepetit, C.2
McGrath, D.V.3
Novak, B.M.4
Grubbs, R.H.5
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34
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20644443971
-
-
Ph.D. Thesis, California Institute of Technology
-
Novak, B. M. Ph.D. Thesis, California Institute of Technology, 1989.
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(1989)
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Novak, B.M.1
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35
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4243081008
-
-
Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317-4325.
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(1996)
Organometallics
, vol.15
, pp. 4317-4325
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Mohr, B.1
Lynn, D.M.2
Grubbs, R.H.3
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36
-
-
0032564844
-
-
Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627-1628.
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(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 1627-1628
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Lynn, D.M.1
Mohr, B.2
Grubbs, R.H.3
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37
-
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0030994105
-
-
Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 779, 3887-3897.
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(1997)
J. Am. Chem. Soc.
, vol.779
, pp. 3887-3897
-
-
Dias, E.L.1
Nguyen, S.T.2
Grubbs, R.H.3
-
38
-
-
33847509883
-
-
In certain cases, the use of 5 mol % 2 in the RCM of 4 gives up to 5% product. The use of alkylidene 3 or increased loading of alkylidene 2 affords no increase in conversion
-
In certain cases, the use of 5 mol % 2 in the RCM of 4 gives up to 5% product. The use of alkylidene 3 or increased loading of alkylidene 2 affords no increase in conversion.
-
-
-
-
39
-
-
0001263185
-
-
and references therein
-
Fu, G. C.; Grubbs, K. H. J. Am. Chem. Soc. 1992, 114, 5426-5427, and references therein.
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(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 5426-5427
-
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Fu, G.C.1
Grubbs, K.H.2
-
40
-
-
0001354464
-
-
Kim, S. H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081.
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(1996)
J. Org. Chem.
, vol.61
, pp. 1073-1081
-
-
Kim, S.H.1
Zuercher, W.J.2
Bowden, N.B.3
Grubbs, R.H.4
-
41
-
-
85022455957
-
-
and references therein
-
Forbes, M. D. E.; Patton, J. T.; Myers, T. L.; Maynard, H. D.; Smith, D. W.; Schulz, G. R.; Wagener, K. B. J. Am. Chem. Soc. 1992, 114, 10978-10980 and references therein.
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(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10978-10980
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Forbes, M.D.E.1
Patton, J.T.2
Myers, T.L.3
Maynard, H.D.4
Smith, D.W.5
Schulz, G.R.6
Wagener, K.B.7
-
42
-
-
33847528553
-
-
John Wiley and Sons: New York, 2nd ed.
-
For a general procedure for malonate alkylation, see: Gilman, H.; Blatt, A. H. Organic Syntheses, Coll. Vol. I; John Wiley and Sons: New York, 2nd ed., 250-251.
-
Organic Syntheses, Coll.
, vol.1
, pp. 250-251
-
-
Gilman, H.1
Blatt, A.H.2
-
43
-
-
0001609007
-
-
and references therein
-
For a discussion of the effects of substrate homologation on intramolecular cyclizations, see: Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232 and references therein.
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(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 224-232
-
-
Jung, M.E.1
Gervay, J.2
-
44
-
-
33847530627
-
-
Another factor that should be considered is substrate dimerization, but this does not appear to be significant in the RCM of 10 as conversion is not dependent on substrate concentration
-
Another factor that should be considered is substrate dimerization, but this does not appear to be significant in the RCM of 10 as conversion is not dependent on substrate concentration.
-
-
-
-
45
-
-
20644466496
-
-
note
-
In the synthesis of unsymmetrical olefins with this methodology, it is critical that the phenyl substituent be placed on the more substituted olefin as in substrate 11. If the phenyl substituent is placed on the less substituted olefin, the ruthenium carbene will preferentially react with the 1,2-disubstituted olefin, then react with the gemdisubstituted olefin intramolecularly, giving one equivalent of cyclized product and the unstable methylidene.
-
-
-
-
46
-
-
20644460864
-
-
note
-
3-. See ref 16.
-
-
-
-
49
-
-
37049113731
-
-
Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1984, 1745-1754.
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J. Chem. Soc., Perkin Trans.
, pp. 1745-1754
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Grigg, R.1
Malone, J.F.2
Mitchell, T.R.B.3
Ramasubbu, A.4
Scott, R.M.5
-
55
-
-
20644434441
-
-
Tropsha, A. E.; Nizhinni, S. V.; Yaguzhinskii, L. S. Bioorg. Khim. 1985,11, 1931-1941.
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(1985)
Bioorg. Khim.
, vol.11
, pp. 1931-1941
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Tropsha, A.E.1
Nizhinni, S.V.2
Yaguzhinskii, L.S.3
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56
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0002714675
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Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978,43, 2923.
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J. Org. Chem.
, vol.43
, pp. 2923
-
-
Still, W.C.1
Kahn, M.2
Mitra, A.3
-
59
-
-
33847506679
-
-
1H NMR. This did not affect the behavior of 11 and was discounted
-
1H NMR. This did not affect the behavior of 11 and was discounted.
-
-
-
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