-
1
-
-
0036522941
-
-
For a general review, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
-
(2002)
Chem. Rev.
, vol.102
, pp. 813
-
-
Aubert, C.1
Buisine, O.2
Malacria, M.3
-
2
-
-
33645392287
-
-
For three typical applications, see: (b) Pauson-Khand reaction: Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominquez, G.; Perez-Castalls, J. Chem. Soc. Rev. 2004, 33, 6285.
-
(2004)
J. Chem. Soc. Rev.
, vol.33
, pp. 6285
-
-
Blanco-Urgoiti, J.1
Anorbe, L.2
Perez-Serrano, L.3
Dominquez, G.4
Perez-Castalls5
-
4
-
-
12744278006
-
-
and references therein
-
(d) [4 + 2 + 2] cycloadditions: Evans, P. A.; Baum, E. W.; Fazal, A. N.; Pink, M. Chem. Commun. 2005, 63 and references therein.
-
(2005)
Chem. Commun.
, pp. 63
-
-
Evans, P.A.1
Baum, E.W.2
Fazal, A.N.3
Pink, M.4
-
6
-
-
0028330334
-
-
(b) Casalnuovo, J. A.; Scott, R. W.; Harwood, E. A.; Schore, N. E. Tetrahedron Lett. 1994, 35, 1153.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 1153
-
-
Casalnuovo, J.A.1
Scott, R.W.2
Harwood, E.A.3
Schore, N.E.4
-
7
-
-
0028905975
-
-
(c) Pagenkopf, B. L.; Lund, E. C.; Livinghouse, T. Tetrahedron 1995, 51, 4421.
-
(1995)
Tetrahedron
, vol.51
, pp. 4421
-
-
Pagenkopf, B.L.1
Lund, E.C.2
Livinghouse, T.3
-
8
-
-
0037459728
-
-
(d) Barriault, L.; Thomas, J. D. O.; Clement, R. J. Org. Chem. 2003, 68, 2317.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 2317
-
-
Barriault, L.1
Thomas, J.D.O.2
Clement, R.3
-
10
-
-
0001284819
-
-
(b) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 12976
-
-
Wender, P.A.1
Jesudason, C.D.2
Nakahira, H.3
Tamura, N.4
Tebbe, A.L.5
Ueno, Y.6
-
11
-
-
0042931243
-
-
(c) Kim, H.; Choi, W. J.; Jung, J.; Kim, S.; Kim, D. J. Am. Chem. Soc. 2003, 125, 10238.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10238
-
-
Kim, H.1
Choi, W.J.2
Jung, J.3
Kim, S.4
Kim, D.5
-
12
-
-
0035967778
-
-
(d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4679.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 4679
-
-
Jaber, J.J.1
Mitsui, K.2
Rychnovsky, S.D.3
-
13
-
-
33645410117
-
-
For alternative methods, see: (e) Mukai, C.; Kim, J. S.; Uchiyama, M.; Sakamoto, S.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1998, 2093.
-
(1998)
J. Chem. Soc., Perkin Trans. 1
, pp. 2093
-
-
Mukai, C.1
Kim, J.S.2
Uchiyama, M.3
Sakamoto, S.4
Hanaoka, M.5
-
14
-
-
0142217511
-
-
(f) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. Tetrahedron 2003, 59, 8889.
-
(2003)
Tetrahedron
, vol.59
, pp. 8889
-
-
Zacuto, M.J.1
O'Malley, S.J.2
Leighton, J.L.3
-
16
-
-
0345967842
-
-
(h) Gaunt, M. J.; Jessiman, A. S.; Orsini, P.; Tanner, H. R.; Hook, D. F.; Ley, S. V. Org. Lett. 2003, 5, 4819.
-
(2003)
Org. Lett.
, vol.5
, pp. 4819
-
-
Gaunt, M.J.1
Jessiman, A.S.2
Orsini, P.3
Tanner, H.R.4
Hook, D.F.5
Ley, S.V.6
-
17
-
-
0034680552
-
-
Lautens, M.; Ouellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 4079
-
-
Lautens, M.1
Ouellet, S.G.2
Raeppel, S.3
-
18
-
-
0006170068
-
-
Lautens, M.; Maddess, M. L.; Sauer, E. L. O.; Ouellet, S. G. Org. Lett. 2002, 4, 83.
-
(2002)
Org. Lett.
, vol.4
, pp. 83
-
-
Lautens, M.1
Maddess, M.L.2
Sauer, E.L.O.3
Ouellet, S.G.4
-
19
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0037474617
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A similar indium-mediated transformation has been developed by Pae that includes a few examples for synthesis of homoallylic homopropargylic alcohols, albeit as mixtures of addition products; see: Oh, B. K.; Cha, J. H.; Cho, Y. S.; Choi, K. I.; Koh, H. Y.; Chang, M. H.; Pae, A. N. Tetrahedron Lett. 2003, 44, 2911.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 2911
-
-
Oh, B.K.1
Cha, J.H.2
Cho, Y.S.3
Choi, K.I.4
Koh, H.Y.5
Chang, M.H.6
Pae, A.N.7
-
20
-
-
0027452721
-
-
See references cited in the following works: (a) Brown, H. C.; Khire, U. R.; Racherla, U. S. Tetrahedron Lett. 1993, 34, 15.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 15
-
-
Brown, H.C.1
Khire, U.R.2
Racherla, U.S.3
-
21
-
-
0001060904
-
-
(b) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 544
-
-
Brown, H.C.1
Khire, U.R.2
Narla, G.3
Racherla, U.S.4
-
22
-
-
0001138389
-
-
(a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 499
-
-
Brown, H.C.1
Dhar, R.K.2
Ganesan, K.3
Singaram, B.4
-
23
-
-
33645386172
-
-
(b) Brown, H. C.; Ravindran, N.; Kulkarni, S. U. J. Org. Chem. 1979, 44, 1979.
-
(1979)
J. Org. Chem.
, vol.44
, pp. 1979
-
-
Brown, H.C.1
Ravindran, N.2
Kulkarni, S.U.3
-
26
-
-
0343483025
-
-
Hopf, H.; Bohm, I.; Kleinschroth, J. Org. Synth. 1982, 60, 41.
-
(1982)
Org. Synth.
, vol.60
, pp. 41
-
-
Hopf, H.1
Bohm, I.2
Kleinschroth, J.3
-
28
-
-
33751553194
-
-
Brown, H. C.; Racherla, U. S.; Pellechia, P. J. J. Org. Chem. 1990, 55, 1868.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 1868
-
-
Brown, H.C.1
Racherla, U.S.2
Pellechia, P.J.3
-
29
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33645381983
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note
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It is not recommended that reaction times extend past 4 h since THF is observed to polymerize slowly under the reaction conditions, making workup problematic.
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30
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33645385195
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note
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THF solutions of 1 were estimated to be approximately 0.8 M after dilution with a volume calculated from the crude mass to afford a 1.0 M solution. There was no noticeable improvement in yield in the optimization studies between 1.5 and 2.0 equiv of 1.
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32
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33645413258
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note
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Borane 33 is reported to give selective reaction on the Re face of the elctrophile.
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33
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33645415290
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Refer to Supporting Information
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Refer to Supporting Information.
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37
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0032477322
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(d) Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12365
-
-
Hua, R.1
Shimada, S.2
Tanaka, M.3
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