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1
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0002110351
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For general reviews of the Diels-Alder Reaction
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0000048258
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TROST, B.M., FLEMING, I., PAQUETTE, L.A., Eds. Pergamon: Oxford
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84890623021
-
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For a detailed discussion of the various modes of complexation, as well as additional methods developed for the Diels-Alder reactions see ref. 1(a) and pertinent references therein.
-
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-
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8
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0010589404
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For lead references see: Iron
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For lead references see: Iron: CARBONARO, A.; GRECO, A.; DALL'ASTA, G.J. Org. Chem. 1968, 33, 3948.
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MATSUDA, I.; SHIBATA, M.; SATO, S.; IZUMI, Y.Tetrahedron Lett. 1987, 28, 3361.
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Matsuda, I.1
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11
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37049093744
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Pd
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Pd: GRENOUILLET, P.; NEIBECKER, D.; TKATCHENKO, I.J. Chem. Soc., Chem. Commun. 1983, 542.
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0000730740
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Ti, pertinent references therein
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Ti: MARCH, K.; ANTROPIUSOVA, H.; PETRUSOVA, L.; TURECEK, F.; HANUS, V.J. Organomet. Chem. 1985, 289, 331 and pertinent references therein.
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MATSUDA, I.; SHIBATA, M.; SATO, S.; IZUMI, Y.Tetrahedron Lett. 1987, 28, 3361.
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Matsuda, I.1
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84940643310
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DIECK, H.T.; DIERCKS, R.Angew. Chem, Int. Ed. Engl. 1983, 22, 778.
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0000257154
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PAIK, S.-J.; SON, S.U.; CHUNG, Y. K.Org. Lett. 1999, 2, 2045.
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17
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0031708442
-
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For a complete list of examples
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For a complete list of examples see: MURAKAMI, M.; UBUKATA, M.; ITAMI, K.; ITO, Y.Angew. Chem, Int. Ed. Engl. 1998, 37, 2248.
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0001230097
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JOLLY, R.S.; LUEDTKE, G.; SHEEHAN, D.; LIVINGHOUSE, T.J. Am. Chem. Soc.1990, 222, 4965.
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19
-
-
33845185652
-
-
The first and only intramolecular transition metal-catalyzed reaction developed prior to this discovery was Ni(0)-catalyzed
-
The first and only intramolecular transition metal-catalyzed reaction developed prior to this discovery was Ni(0)-catalyzed: WENDER, P.A.; JENKINS, T. E.J. Am. Chem. Soc. 1989, 222, 6432.
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Wender, P.A.1
Jenkins, T.E.2
-
20
-
-
84890599392
-
-
The observed stereoselectivity matches that of the corresponding thermal reaction, for which only 20 product was observed after heating to 120°C for 3 days. Additionally, simple acid catalyst effects were ruled out by exposing the starting ether (21)to 0.1 equiv HCl over 1 h under optimized reaction conditions, in the absence of rhodium catalyst. Under these conditions the starting material was recovered unchanged.
-
-
-
-
21
-
-
84890678441
-
-
This intermediate is also often depicted as an η3-type intermediate.
-
-
-
-
22
-
-
0000829328
-
-
Pronounced rate and selectivity enhancements had previously been observed for Ni(0)-catalyzed cyclodimerizations as well as rhodium-catalyzed alkene hydroformylation reactions. For related references see: (Ni)
-
Pronounced rate and selectivity enhancements had previously been observed for Ni(0)-catalyzed cyclodimerizations as well as rhodium-catalyzed alkene hydroformylation reactions. For related references see: (Ni) VAN LEEUWEN, P.W.N.M.; ROOBEEK, CF.Tetrahedron 1981, 37, 1973.
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Van Leeuwen, P.W.N.M.1
Roobeek, C.F.2
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24
-
-
84890716680
-
-
Ph.D. thesis, University of Delaware, Newark, Delaware 19713, or "Recent advances in Rh-catalyzed carbocycli-zation reactions"
-
For a complete and detailed discussion see JOHN.E. ROBINSON, Ph.D. thesis, University of Delaware, Newark, Delaware 19713, or "Recent advances in Rh-catalyzed carbocycli-zation reactions" John E. Robinson, http:// www.chem.wayne.edu/acs-organic-division/fellowships.html.
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Robinson, J.E.1
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25
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0000551283
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WENDER, P.A.; JENKINS, T. E.; SUZUKI, S.J. Am. Chem. Soc. 1995, 227, 1843.
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Wender, P.A.1
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Suzuki, S.3
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26
-
-
18444393960
-
-
There are numerous examples of rhoda-cycle-propene type intermediates in the literature, suggesting that the modified Magnus-Buchwald type of transition state may be quite feasible. For lead references see
-
There are numerous examples of rhoda-cycle-propene type intermediates in the literature, suggesting that the modified Magnus-Buchwald type of transition state may be quite feasible. For lead references see: BUCKNER, S.W.; FREISER, B.S.Polyhedron 1989, 8, 1401.
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Buckner, S.W.1
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28
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84890683853
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and references cited therein
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TOLBERT, M.A.; MANDICH, M.L.; HALLE, L. F.; BEAUCHAMP, J. L.J. Am. Chem. Soc., 208, 5675 and references cited therein.
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RAJANBABU, T.V.; AYERS, T.A.; HALLIDAY, G.A.; YOU, K. K.; CALABRESE, J.C.J. Org. Chem. 1997, 62, 6012.
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BURK, M.J.; FEASTER, J.E.; NUGENT, W.A.; HARLOW, R.L.J. Am. Chem. Soc. 1993, 225, 10 125.
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36
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-
84890665683
-
-
This general strategy of activating the rho-dium(I) complex through hydrogenation of the dialkene complex was previously utilized by Bosnich and co-workers to enhance the rate of hydroacylation in the corresponding rhodium(I)-catalyzed transformation. For lead references see ref. 15 and pertinent references therein.
-
-
-
-
37
-
-
84890620858
-
-
This catalyst system was also applied to the [5 + 2] carbocyclization reactions, discussed at length in Chapter 13 of this book.
-
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38
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0034649134
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WANG, B.; CAO, P.; ZHANG, X.Tetrahedron Lett. 2000, 42, 8041.
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GILBERTSON, S.R.; HOGE, G.S.; GENOV, D.G.J. Org. Chem. 1998, 63, 10077.
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41
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-
84890781991
-
-
Livinghouse and co-workers report a similar carbocyclization, using a dimethyl malonate diene-ene derivative, in which they obtained 6ee(69) with a highly sterically hindered DIOP-based ligand (ref. 25). The unaltered DIOP ligand was also highly efficient (83), but imparted poor enantio- control (10 ee).
-
-
-
-
42
-
-
0026721571
-
-
To date there are more than 100 cyclo-octanoid-containing natural products. For a lead reference concerning this statistic, see
-
To date there are more than 100 cyclo-octanoid-containing natural products. For a lead reference concerning this statistic, see: PETASIS, N.A.; PATANE, M.A.Tetrahedron 1992, 48, 5757.
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Petasis, N.A.1
Patane, M.A.2
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43
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0029968239
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For recent review of metal-mediated synthesis of cyclooctanoids see
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For recent review of metal-mediated synthesis of cyclooctanoids see: SIEBURTH, S.MCN.; CUNARD, T.Tetrahedron 1996, 52, 6251.
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YET, L.Chem. Rev. 2000, 200, 2963.
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47
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0004029968
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For lead references concerning the [4+ 4] intermolecular cyclizations see, Academic Press, New York
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For lead references concerning the [4+ 4] intermolecular cyclizations see: JOLLY, P.W.; WILKE, G.inThe Organic Chemistry of Nickel, Vol. 2. Academic Press, New York, 1975.
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JOLLY, P.W., TKATCHENKO, I., WILKE, G.Angew. Chem., Int. Ed. Engl. 1971, 20, 329.
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84982074856
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BOGDANOVIC, B.; HEIMBACH, P.; KRÖNER, M.; WILKE, G.; HOFFMANN, E.G.; BRANDT, J.Justus Liebigs Ann. Chem. 1969, 727, 143.
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50
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0034601016
-
-
Other transition metal complexes also catalyzed the dimerization of simple butadiene type substrates. For related examples see
-
Other transition metal complexes also catalyzed the dimerization of simple butadiene type substrates. For related examples see: BOSCH, M.; BROOKHART, M.S.; ILG, K.; WERNER, H.Angew. Chem., Int. Ed. Engl. 2000, 39, 2304.
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51
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0000104671
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and references cited therein
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Nagashima, H.6
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52
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0001466031
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For lead references on intramolecular [4+ 4] cyclization reactions see
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For lead references on intramolecular [4+ 4] cyclization reactions see: WENDER, P.A.; IHLE, N.C.J. Am. Chem. Soc. 1986, 208, 4678.
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WENDER, P.A.; IHLE, N.C.; CORREIA, C. R.J. Am. Chem. Soc. 1988, 220, 5904.
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Correia, C.R.3
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56
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0000723880
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For lead references pertaining to iron- and cobalt-catalyzed [4+ 2 + 2] intermolecular cyclizations see
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For lead references pertaining to iron- and cobalt-catalyzed [4+ 2 + 2] intermolecular cyclizations see: GRECO, A.; CARBONARO, A.; DALL'ASTA, G.J. Org. Chem. 1970, 35, 271.
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0000095446
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For the cobalt-catalyzed [4+2 +2] intramolecular cyclization see
-
For the cobalt-catalyzed [4+2 +2] intramolecular cyclization see: LAUTENS, M.; TAM, W.; LAUTENS, J.C.; EDWARDS, L.G.; CRUDDEN, CM.; SMITH, A.C.J. Am. Chem. Soc.1995, 227, 6863.
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EVANS, P.A.; ROBINSON, J.E.; BAUM, E.W.; FAZAL, A.N.J. Am. Chem. Soc. 2002, 224, 8782.
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Fazal, A.N.4
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63
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84890742169
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-
Attempts to assign the relative configuration of the homodimer were complicated due to the extreme instability of the compound. Additionally, due to the increased reactivity of this substrate for homo-dimerization, there was no noticeable concentration effect between 0.1 and 0.0626 M.
-
-
-
-
64
-
-
0034601016
-
-
The following [2 +2 +2] product was isolated as a single regioisomer
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BOSCH, M.; BROOKHART, M.S.; ILG, K.; WERNER, H.Angew. Chem., Int. Ed. Engl. 2000, 39, 2304.
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65
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0001758174
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For the related use of a temporary sulfur tether in Pauson-Khand reactions see
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For the related use of a temporary sulfur tether in Pauson-Khand reactions see: CASTRO, J.; MOYANO, A.; PERICAS, M.A.; RIERA, A.J. Org. Chem. 1998, 63, 3346.
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