-
2
-
-
33745353059
-
-
P. A. Wender, M. P. Croatt, B. Witulski, Tetrahedron 2006, 62, 7505-7511;
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(2006)
Tetrahedron
, vol.62
, pp. 7505-7511
-
-
Wender, P.A.1
Croatt, M.P.2
Witulski, B.3
-
3
-
-
0036291655
-
-
P. A. Wender, F. C. Bi, G. G. Gamber, F. Gosselin, R. D. Hubbard, M. J. C. Scanio, R. Sun, T. J. Williams, L. Zhang, Pure Appl. Chem. 2002, 74, 25-31;
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(2002)
Pure Appl. Chem
, vol.74
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-
Wender, P.A.1
Bi, F.C.2
Gamber, G.G.3
Gosselin, F.4
Hubbard, R.D.5
Scanio, M.J.C.6
Sun, R.7
Williams, T.J.8
Zhang, L.9
-
5
-
-
0002466970
-
-
Ed, T. Hudlicky, JAI Press, Greenwich
-
P. A. Wender, B. L. Miller, Organic Synthesis: Theory and Applications, Vol. 2 (Ed.: T. Hudlicky), JAI Press, Greenwich, 1993, pp. 27-66.
-
(1993)
Organic Synthesis: Theory and Applications
, vol.2
, pp. 27-66
-
-
Wender, P.A.1
Miller, B.L.2
-
7
-
-
84933051845
-
-
W. Reppe, O. Schlichting, K. Klager, T. Toepel, Justus Liebigs Ann. Chem. 1948, 560, 1-92.
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(1948)
Justus Liebigs Ann. Chem
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, pp. 1-92
-
-
Reppe, W.1
Schlichting, O.2
Klager, K.3
Toepel, T.4
-
8
-
-
34447094656
-
-
For a thematic issue on green chemistry, see
-
a) For a thematic issue on green chemistry, see: Chem. Rev. 2007, 107, 2167-2820;
-
(2007)
Chem. Rev
, vol.107
, pp. 2167-2820
-
-
-
9
-
-
0003980673
-
-
For the principles of green chemistry, see:, Oxford University Press, New York
-
For the principles of green chemistry, see: P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998, p. 30;
-
(1998)
Green Chemistry: Theory and Practice
, pp. 30
-
-
Anastas, P.T.1
Warner, J.C.2
-
10
-
-
73349120413
-
-
For more information, visit the ACS Green Chemistry Institute at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html? DOC= greenchemistryinstitute\index.html.
-
For more information, visit the ACS Green Chemistry Institute at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html? DOC= greenchemistryinstitute\index.html.
-
-
-
-
11
-
-
70349769724
-
-
For a recent discussion of redox economy, see
-
For a recent discussion of redox economy, see: N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. Int. Ed. 2009, 48, 2854-2867.
-
(2009)
Angew. Chem. Int. Ed
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-
Burns, N.Z.1
Baran, P.S.2
Hoffmann, R.W.3
-
12
-
-
51649130191
-
-
and For recent and seminal discussions of atom economy, see
-
a) For recent and seminal discussions of atom economy, see: C.-J. Li, B. M. Trost, Proc. Natl. Acad. Sci. USA 2008, 105, 13197-13202 and
-
(2008)
Proc. Natl. Acad. Sci. USA
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Li, C.-J.1
Trost, B.M.2
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13
-
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0026418434
-
-
B. M. Trost, Science 1991, 254, 1471-1477.
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(1991)
Science
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Trost, B.M.1
-
14
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67749111694
-
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D. A. Nicewicz, A. D. Satterfield, D. C. Schmitt, J. S. Johnson, J. Am. Chem. Soc. 2008, 130, 17281-17283.
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(2008)
J. Am. Chem. Soc
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Nicewicz, D.A.1
Satterfield, A.D.2
Schmitt, D.C.3
Johnson, J.S.4
-
15
-
-
0028956752
-
-
For the first [5+2] reaction of a VCP, see: P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721;
-
a) For the first [5+2] reaction of a VCP, see: P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721;
-
-
-
-
16
-
-
0032576188
-
-
For the first intermolecular [5+2] reaction, see: P. A. Wender, H. Rieck, M. Fuji, J. Am. Chem. Soc. 1998, 120, 10976-10977;
-
For the first intermolecular [5+2] reaction, see: P. A. Wender, H. Rieck, M. Fuji, J. Am. Chem. Soc. 1998, 120, 10976-10977;
-
-
-
-
17
-
-
0032543523
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-
For the first [5+2] reaction with an alkene, see: P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, N. Pleuss, Tetrahedron 1998, 54, 7203-7220;
-
For the first [5+2] reaction with an alkene, see: P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, N. Pleuss, Tetrahedron 1998, 54, 7203-7220;
-
-
-
-
18
-
-
0033538287
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-
For the first [5+2] reaction with allenes, see: P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349;
-
For the first [5+2] reaction with allenes, see: P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349;
-
-
-
-
19
-
-
18644375951
-
-
For the first intermolecular [5+2] reaction with allenes, see: H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531;
-
For the first intermolecular [5+2] reaction with allenes, see: H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531;
-
-
-
-
20
-
-
0037176267
-
-
For the first [5+2] reaction with cyclopropyl imines, see: P. A. Wender, T. M. Pedersen, M. J. C. Scanio, J. Am. Chem. Soc. 2002, 124, 15154-15155.
-
For the first [5+2] reaction with cyclopropyl imines, see: P. A. Wender, T. M. Pedersen, M. J. C. Scanio, J. Am. Chem. Soc. 2002, 124, 15154-15155.
-
-
-
-
21
-
-
0002857049
-
-
a) I. Ryu, K. Ikura, Y. Tamura, J. Maenaka, A. Ogawa, N. Sonoda, Synlett., 1994, 941-942;
-
(1994)
Synlett
, pp. 941-942
-
-
Ryu, I.1
Ikura, K.2
Tamura, Y.3
Maenaka, J.4
Ogawa, A.5
Sonoda, N.6
-
24
-
-
0011650374
-
-
R. G. Salomon, M. F. Salomon, J. L. C. Kachinski, J. Am. Chem. Soc. 1977, 99, 1043-1054;
-
(1977)
J. Am. Chem. Soc
, vol.99
, pp. 1043-1054
-
-
Salomon, R.G.1
Salomon, M.F.2
Kachinski, J.L.C.3
-
27
-
-
3342979429
-
-
For computational analysis of the mechanism of the [5+2] reaction using density functional theory, see: Z.-X. Yu, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 9154-9155.
-
For computational analysis of the mechanism of the [5+2] reaction using density functional theory, see: Z.-X. Yu, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 9154-9155.
-
-
-
-
28
-
-
0034674966
-
-
P. A. Wender, A. G. Correa, Y. Sato, R. Sun, J. Am. Chem. Soc. 2000, 122, 7815-7816.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 7815-7816
-
-
Wender, P.A.1
Correa, A.G.2
Sato, Y.3
Sun, R.4
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29
-
-
33746278459
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-
For a [6+1] reaction allenylcyclobutanes, see: P. A. Wender, N. M. Deschamps, R. Sun, Angew. Chem. Int. Ed. 2006, 45, 3957-3960;
-
a) For a [6+1] reaction allenylcyclobutanes, see: P. A. Wender, N. M. Deschamps, R. Sun, Angew. Chem. Int. Ed. 2006, 45, 3957-3960;
-
-
-
-
30
-
-
29244440374
-
-
For the carbonylative rearrangement of allenic ethers, see
-
For the carbonylative rearrangement of allenic ethers, see: P. A. Wender, N. M. Deschamps, R. Sun, Can. J. Chem. 2005, 83, 838-842.
-
(2005)
Can. J. Chem
, vol.83
, pp. 838-842
-
-
Wender, P.A.1
Deschamps, N.M.2
Sun, R.3
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31
-
-
33845203735
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-
P. A. Wender, T. J. Paxton, T. J. Williams, J. Am. Chem. Soc. 2006, 128, 14814-14815.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 14814-14815
-
-
Wender, P.A.1
Paxton, T.J.2
Williams, T.J.3
-
32
-
-
0037181346
-
-
P. A. Wender, G. G. Gamber, R. D. Hubbard, L. Zhang, J. Am. Chem. Soc. 2002, 124, 2876-2877.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 2876-2877
-
-
Wender, P.A.1
Gamber, G.G.2
Hubbard, R.D.3
Zhang, L.4
-
33
-
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14844290896
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-
P. A. Wender, G. G. Gamber, R. D. Hubbard, S. M. Pham, L. Zhang, J. Am. Chem. Soc. 2005, 127, 2836-2837.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 2836-2837
-
-
Wender, P.A.1
Gamber, G.G.2
Hubbard, R.D.3
Pham, S.M.4
Zhang, L.5
-
36
-
-
0001230097
-
-
For related subsequent reports by Livinghouse and Wender using alkenes and allenes, see: b
-
For related subsequent reports by Livinghouse and Wender using alkenes and allenes, see: b) R. S. Jolly, G. Luedtke, D. Sheehan, T. Livinghouse, J. Am. Chem. Soc. 1990, 112, 4965-4966;
-
(1990)
J. Am. Chem. Soc
, vol.112
, pp. 4965-4966
-
-
Jolly, R.S.1
Luedtke, G.2
Sheehan, D.3
Livinghouse, T.4
-
37
-
-
0000551283
-
-
P. A. Wender, T. E. Jenkins, S. Suzuki, J. Am. Chem. Soc. 1995, 117, 1843-1844.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 1843-1844
-
-
Wender, P.A.1
Jenkins, T.E.2
Suzuki, S.3
-
38
-
-
73349117650
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-
For the trapping of intermediates in the [4+2] reaction with an alkyne to achieve a [4+2+2] reaction, see: P. A. Wender, J. P. Christy, J. Am. Chem. Soc. 2006, 128, 6530-6531.
-
For the trapping of intermediates in the [4+2] reaction with an alkyne to achieve a [4+2+2] reaction, see: P. A. Wender, J. P. Christy, J. Am. Chem. Soc. 2006, 128, 6530-6531.
-
-
-
-
39
-
-
0037693723
-
-
For the intramolecular diene-yne [4+2+1] and [2+2+1] reactions, see P. A. Wender, N. M. Deschamps, G. G. Gamber, Angew. Chem. Int. Ed. 2003, 42, 1853-1857;
-
a) For the intramolecular diene-yne [4+2+1] and [2+2+1] reactions, see P. A. Wender, N. M. Deschamps, G. G. Gamber, Angew. Chem. Int. Ed. 2003, 42, 1853-1857;
-
-
-
-
40
-
-
4143064955
-
-
For the intermolecular dienyl-Pauson-Khand reaction, see
-
For the intermolecular dienyl-Pauson-Khand reaction, see: P. A. Wender, N. M. Deschamps, T. J. Williams, Angew. Chem. Int. Ed. 2004, 43, 3076-3079;
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 3076-3079
-
-
Wender, P.A.1
Deschamps, N.M.2
Williams, T.J.3
-
41
-
-
2442555184
-
-
For the diene-ene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, J. Am. Chem. Soc. 2004, 126, 5948-5949;
-
For the diene-ene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, J. Am. Chem. Soc. 2004, 126, 5948-5949;
-
-
-
-
42
-
-
33746304119
-
-
For the diene-allene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, Angew. Chem. Int. Ed. 2006, 45, 2459-2462.
-
For the diene-allene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, Angew. Chem. Int. Ed. 2006, 45, 2459-2462.
-
-
-
-
43
-
-
33845245890
-
-
For recent reviews including work from the groups of Brummond, Buchwald, Carretero, Chung, Cook, Greene, Jeong, Krafft, Livinghouse, Mitsudo, Murai, Mukai, Narasaka, Periás, Periasamy, Schore, Rautenstrauch, and Yamaguchi, see: a
-
For recent reviews including work from the groups of Brummond, Buchwald, Carretero, Chung, Cook, Greene, Jeong, Krafft, Livinghouse, Mitsudo, Murai, Mukai, Narasaka, Periás, Periasamy, Schore, Rautenstrauch, and Yamaguchi, see: a) T. Shibata, Adv. Synth. Catal. 2006, 348, 2328-2336;
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Adv. Synth. Catal
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Shibata, T.1
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45
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1642284120
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J. Blanc-Urgoiti, L. Anorbe, L. Perez-Serrano, G. Dominguez, J. Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42;
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50
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73349128575
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Albany Molecular Research Inc
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Technical Report No. 18, 4, New York
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L. Yet, Technical Report No. 18, Vol 4, Albany Molecular Research Inc., New York, 2000.
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(2000)
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-
Yet, L.1
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51
-
-
0013265679
-
-
For an example using a stoichiometric organometallic reagent as one of the components in a [4+2+1] reaction, see: J. W. Herndon, G. Chatterjee, P. P. Patel, J. J. Matsi, S. U. Turner, J. J. Harp, M. D. Reid, J. Am. Chem. Soc. 1991, 113, 7808-7809;
-
a) For an example using a stoichiometric organometallic reagent as one of the components in a [4+2+1] reaction, see: J. W. Herndon, G. Chatterjee, P. P. Patel, J. J. Matsi, S. U. Turner, J. J. Harp, M. D. Reid, J. Am. Chem. Soc. 1991, 113, 7808-7809;
-
-
-
-
52
-
-
4544342224
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-
For a metal-catalyzed [4+2+1] reaction of a diene-yne and trimethylsilyldiazomethane subsequently reported, see: J. Montgomery, Y. Ni, J. Am. Chem. Soc. 2004, 126, 11162-11163.
-
For a metal-catalyzed [4+2+1] reaction of a diene-yne and trimethylsilyldiazomethane subsequently reported, see: J. Montgomery, Y. Ni, J. Am. Chem. Soc. 2004, 126, 11162-11163.
-
-
-
-
53
-
-
1442309763
-
-
For subsequent reports of the dienyl-Pauson-Khand reaction, see
-
a) For subsequent reports of the dienyl-Pauson-Khand reaction, see: M.-C. P. Yeh, W.-C. Tsao, J.-S. Ho, C.-C. Tai, D.-Y. Chiou, L.-H. Tu, Organometallics 2004, 23, 792-799;
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Yeh, M.-C.P.1
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Chiou, D.-Y.5
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54
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33645016024
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K. H. Park, S. Y. Choi, S. Y. Kim, Y. K. Chung, Synlett., 2006, 4, 527-532;
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Park, K.H.1
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Kim, S.Y.3
Chung, Y.K.4
-
55
-
-
73349094529
-
-
For an initially reported [3+2+1] reaction that was corrected to be a diene-ene [2+2+1] reaction, see: Y. K. Chung, S. I. Lee, J. H. Park, S.-G. Lee, J. Am. Chem. Soc. 2004, 126, 10190
-
For an initially reported [3+2+1] reaction that was corrected to be a diene-ene [2+2+1] reaction, see: Y. K. Chung, S. I. Lee, J. H. Park, S.-G. Lee, J. Am. Chem. Soc. 2004, 126, 10190
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56
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1542287652
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[J. Am. Chem. Soc. 2004, 126, 2714-2715].
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57
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37049132156
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For the first report, see
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a) For the first report, see: I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, J. Chem. Soc., Chem. Commun. 1971, 36;
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58
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0034638410
-
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For a report of an enantioselective intermolecular Pauson-Khand reaction, see
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For a report of an enantioselective intermolecular Pauson-Khand reaction, see: T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852-9853;
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59
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18844403627
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For a review of components in the intermolecular Pauson-Khand reaction, see
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For a review of components in the intermolecular Pauson-Khand reaction, see: S. E. Gibson, N. Mainolfi, Angew. Chem. Int. Ed. 2005, 44, 3022-3037.
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60
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0001383865
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For a seminal contribution, see
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a) For a seminal contribution, see: M. E. Krafft, J. Am. Chem. Soc. 1988, 110, 968-970;
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Krafft, M.E.1
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61
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4444362831
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For a more recent example, see
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For a more recent example, see: K. Itami, K. Mitsudo, K. Fujita, Y. Ohashi, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 11058-11066.
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J. Am. Chem. Soc
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T. Kobayashi, Y. Koga, K. Narasaka, J. Organomet. Chem. 2001, 624, 73-87.
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0001141704
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E. Negishi, D. Choueiry, T. B. Nguyen, D. R. Swanson, N Suzuki, T. Takahashi, J. Am. Chem. Soc. 1994, 116, 9751-9752.
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66
-
-
73349124331
-
-
The authors report trans-fusion of the rings of 50 based on NOESY crosspeaks; however, the spectroscopic data for 50 match those of 55, which appears to have cis-fusion of the rings based on strong 1D nOe enhancement between the two angular hydrogen atoms. Importantly, the diastereotopic methyl peaks from the malonate tether in 49 appear as a 6-hydrogen singlet in the 1H NMR spectrum although the 1H NMR spectrum of 50 and all analogous products formed from the diene-ene [2+2+1] reaction with a malonate tether have significant separation of the two methyl peaks. Based on this data, it appears that 50 is incorrectly assigned and is actually cis-fused and that 49 is correctly assigned as the trans-fused bicycle.
-
The authors report trans-fusion of the rings of 50 based on NOESY crosspeaks; however, the spectroscopic data for 50 match those of 55, which appears to have cis-fusion of the rings based on strong 1D nOe enhancement between the two angular hydrogen atoms. Importantly, the diastereotopic methyl peaks from the malonate tether in 49 appear as a 6-hydrogen singlet in the 1H NMR spectrum although the 1H NMR spectrum of 50 and all analogous products formed from the diene-ene [2+2+1] reaction with a malonate tether have significant separation of the two methyl peaks. Based on this data, it appears that 50 is incorrectly assigned and is actually cis-fused and that 49 is correctly assigned as the trans-fused bicycle.
-
-
-
-
67
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3142697763
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73349091682
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It should be noted that in ref.[32b, 10 mol, catalyst was reported to have a 73% yield on the gram-scale, but ref.[32a] was run with stoichiometric catalyst loading on a 4.9 kilogram scale
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[32a] was run with stoichiometric catalyst loading on a 4.9 kilogram scale.
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74
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I- catalyzed allenic Pauson-Khand reaction based on DFT calculations, see: A. S. Bayden, K. M. Brummond, K. D. Jordan, Organometallics 2006, 25, 5204-5206.
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I- catalyzed allenic Pauson-Khand reaction based on DFT calculations, see: A. S. Bayden, K. M. Brummond, K. D. Jordan, Organometallics 2006, 25, 5204-5206.
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This step would additionally involve conversion of the dimeric rhodium catalyst into two monomeric rhodium catalysts. This is presumably facile in the presence of dienes
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This step would additionally involve conversion of the dimeric rhodium catalyst into two monomeric rhodium catalysts. This is presumably facile in the presence of dienes.
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84
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This structure could be an intermediate or the transition state between two intermediates with rhodium coordinated to either the alpha or beta face of the alkene
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This structure could be an intermediate or the transition state between two intermediates with rhodium coordinated to either the alpha or beta face of the alkene.
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