-
1
-
-
0000051366
-
-
For lead references on the isolation of 1-6, see: (a) 1. San Feliciano, A.; Barrero, A. F.; Medarde, M.; Miguel del Corral, J. M.; Aramburu, A. Tetrahedron Lett. 1985, 26, 2369.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 2369
-
-
San Feliciano, A.1
Barrero, A.F.2
Medarde, M.3
Miguel Del Corral, J.M.4
Aramburu, A.5
-
2
-
-
0001180034
-
-
(b) 2. Adesomoju, A. A.; Okogun, J. I.; Cava, M. P.; Carroll, P. J. Phytochemistry 1983, 22, 2535.
-
(1983)
Phytochemistry
, vol.22
, pp. 2535
-
-
Adesomoju, A.A.1
Okogun, J.I.2
Cava, M.P.3
Carroll, P.J.4
-
3
-
-
0001190429
-
-
(c) 3. Enoki, N.; Furusaki, A.; Suehiro, K.; Ishida, R.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 4341.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 4341
-
-
Enoki, N.1
Furusaki, A.2
Suehiro, K.3
Ishida, R.4
Matsumoto, T.5
-
6
-
-
0029968239
-
-
For recent reviews on metal-mediated cyclooctanoid construction, see: (a) (b) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251.
-
(1996)
Tetrahedron
, vol.52
, pp. 6251
-
-
Sieburth, S.McN.1
Cunard, N.T.2
-
8
-
-
0034246704
-
-
(c) Yet, L. Chem. Rev. 2000, 100, 2963.
-
(2000)
Chem. Rev.
, vol.100
, pp. 2963
-
-
Yet, L.1
-
9
-
-
0036522941
-
-
For recent reviews on metal-catalyzed carbocyclization reactions, 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
-
12
-
-
0012759546
-
-
Lautens, M.; Trost, B. M. Eds.; Georg Thieme Verlag: New York
-
For recent reviews on metal-mediated [2+2+2] carbocyclizations, see: (a) Malacria, M.; Aubert, C.; Renaud J. L. In Science of Synthesis: Houben-Weyl Methods for Molecular Transformations; Lautens, M.; Trost, B. M. Eds.; Georg Thieme Verlag: New York, 2001; Vol 1, pp 439-530.
-
(2001)
Science of Synthesis: Houben-Weyl Methods for Molecular Transformations
, vol.1
, pp. 439-530
-
-
Malacria, M.1
Aubert, C.2
Renaud, J.L.3
-
14
-
-
84890619148
-
-
Evans, P. A. Ed.; Wiley-VCH: Weinheim, Ch. 7, and pertinent references cited therein
-
(c) Fujiwara, M.; Ojima, I. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A. Ed.; Wiley-VCH: Weinheim, 2005; Ch. 7, p 129 and pertinent references cited therein.
-
(2005)
Modern Rhodium-catalyzed Organic Reactions
, pp. 129
-
-
Fujiwara, M.1
Ojima, I.2
-
15
-
-
0037205927
-
-
(a) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 8782
-
-
Evans, P.A.1
Robinson, J.E.2
Baum, E.W.3
Fazal, A.N.4
-
16
-
-
79956200412
-
-
(b) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2003, 125, 14648.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 14648
-
-
Evans, P.A.1
Robinson, J.E.2
Baum, E.W.3
Fazal, A.N.4
-
17
-
-
0037205878
-
-
For another example of a rhodium(I)-catalyzed [4+2+2] carbocyclizations see: Gilbertson, S. R.; DeBeof, B. J. Am. Chem. Soc. 2002, 124, 8784.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 8784
-
-
Gilbertson, S.R.1
DeBeof, B.2
-
18
-
-
0000723880
-
-
For related metal-catalyzed [4+2+2] carbocyclizations reactions, see: (a) Greco, A.; Carbonaro, A.; Dall'Asta, G. J. Org. Chem. 1970, 35, 271.
-
(1970)
J. Org. Chem.
, vol.35
, pp. 271
-
-
Greco, A.1
Carbonaro, A.2
Dall'Asta, G.3
-
19
-
-
0000522063
-
-
(b) Carbonaro, A.; Cambisi, F.; Dall'Asta, G J. Org. Chem. 1971, 36, 1443.
-
(1971)
J. Org. Chem.
, vol.36
, pp. 1443
-
-
Carbonaro, A.1
Cambisi, F.2
Dall'Asta, G.3
-
20
-
-
0000095446
-
-
(c) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 6863
-
-
Lautens, M.1
Tam, W.2
Lautens, J.C.3
Edwards, L.G.4
Crudden, C.M.5
Smith, A.C.6
-
21
-
-
0141520554
-
-
(d) Varela, J. A.; Castedo, L.; Saá, C. Org. Lett. 2003, 5, 2841.
-
(2003)
Org. Lett.
, vol.5
, pp. 2841
-
-
Varela, J.A.1
Castedo, L.2
Saá, C.3
-
22
-
-
0034601016
-
-
The rhodium-catalyzed cycloisomerization of 1,3-butadiene is known to favor oligomerization rather than the formation of cyclooctadiene, see: Bosch, M.; Brookhart, M. S.; Ilg, K.; Werner, H. Angew. Chem., Int. Ed. 2000, 39, 2304.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2304
-
-
Bosch, M.1
Brookhart, M.S.2
Ilg, K.3
Werner, H.4
-
23
-
-
0034641228
-
-
Although the carbocyclization proceeds with heteroatom tethers, the carbon derivatives lead to mixtures, in which enyne cycloisomerization was the major adduct. For a rhodiumcatalyzed version, see: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 6490
-
-
Cao, P.1
Wang, B.2
Zhang, X.3
-
24
-
-
12744278006
-
-
Evans, P. A.; Baum, E. W.; Fazal, A. N.; Pink, M. Chem. Commun. 2005, 63.
-
(2005)
Chem. Commun.
, pp. 63
-
-
Evans, P.A.1
Baum, E.W.2
Fazal, A.N.3
Pink, M.4
-
25
-
-
13644255984
-
-
For a detailed discussion of the mechanism and origin of diastereoselectivity, see Baik, M.-H.; Baum, E. W.; Burland, M. C.; Evans, P. A. J. Am. Chem. Soc. 2005, 127, 1602.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 1602
-
-
Baik, M.-H.1
Baum, E.W.2
Burland, M.C.3
Evans, P.A.4
-
26
-
-
84981776828
-
-
Wanzlick, H.-W.; Schönherr, H.-J. Angew. Chem., Int. Ed. 1968, 7, 141.
-
(1968)
Angew. Chem., Int. Ed.
, vol.7
, pp. 141
-
-
Wanzlick, H.-W.1
Schönherr, H.-J.2
-
28
-
-
0001286592
-
-
Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 361
-
-
Arduengo, A.J.1
Harlow, R.L.2
Kline, M.3
-
30
-
-
0000393279
-
-
(a) Huang, J.; Stevens, E. D. Nolan, S. P. Organometallics 2000, 19, 1194.
-
(2000)
Organometallics
, vol.19
, pp. 1194
-
-
Huang, J.1
Stevens, E.D.2
Nolan, S.P.3
-
31
-
-
0038682047
-
-
(b) Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663.
-
(2003)
Organometallics
, vol.22
, pp. 1663
-
-
Chianese, A.R.1
Li, X.2
Janzen, M.C.3
Faller, J.W.4
Crabtree, R.H.5
-
34
-
-
0345276422
-
-
For an example of a rhodium(I) NHC-catalyzed hydrosilylation/cyclization of 1, 6-enynes, see: Park, K. H.; Kim, S. Y.; Son, S. U.; Chung, Y. K. Eur. J. Org. Chem. 2003, 4341.
-
(2003)
Eur. J. Org. Chem.
, pp. 4341
-
-
Park, K.H.1
Kim, S.Y.2
Son, S.U.3
Chung, Y.K.4
-
35
-
-
0037176243
-
-
(a) For an example of Ni-NHC catalyzed [2+2+2] cycloaddition, see: Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc., 2002, 124, 15188.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 15188
-
-
Louie, J.1
Gibby, J.E.2
Farnworth, M.V.3
Tekavec, T.N.4
-
36
-
-
0348040030
-
-
(b) For an example of Co-NHC catalyzed Pauson Khand reaction, see: Gibson, S. E.; Johnstone, C.; Loch, J. A.; Steed, J. W.; Strevenazzi, A. Organometallics 2003, 22, 5374.
-
(2003)
Organometallics
, vol.22
, pp. 5374
-
-
Gibson, S.E.1
Johnstone, C.2
Loch, J.A.3
Steed, J.W.4
Strevenazzi, A.5
-
37
-
-
0037450462
-
-
Seayad, A. M.; Selvakumar, K.; Ahmed, M.; Bellar, M. Tetrahedron Lett. 2003, 44, 1679.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 1679
-
-
Seayad, A.M.1
Selvakumar, K.2
Ahmed, M.3
Bellar, M.4
-
38
-
-
0037156273
-
-
For a saturated version of the NHC catalyst, see: Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219.
-
(2002)
J. Organomet. Chem.
, vol.649
, pp. 219
-
-
Denk, K.1
Sirsch, P.2
Herrmann, W.A.3
-
40
-
-
0000079538
-
-
Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 2298
-
-
Nishiyama, H.1
Kitajima, T.2
Matsumoto, M.3
Itoh, K.4
-
42
-
-
0141665446
-
-
Fleming, I., Ed.; Georg Thieme Verlag: New York
-
For recent reviews on TST strategies, see: (a) White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: New York, 2001; Vol. 4, p 371.
-
(2001)
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations
, vol.4
, pp. 371
-
-
White, J.D.1
Carter, R.G.2
-
43
-
-
0012759546
-
-
Fleming, I., Ed.; Georg Thieme Verlag: New York, and pertinent references therein
-
(b) Skrydstrup, M. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: New York, 2001; Vol. 4, p 439 and pertinent references therein.
-
(2001)
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations
, vol.4
, pp. 439
-
-
Skrydstrup, M.1
-
44
-
-
3643074061
-
-
For examples of metal-mediated and metal-catalyzed TST carbocyclization reactions, see: (a) Kagoshima, H.; Hayashi, M.; Yukihiko, H.; Saigo, K. Organometallics 1996, 15, 5439.
-
(1996)
Organometallics
, vol.15
, pp. 5439
-
-
Kagoshima, H.1
Hayashi, M.2
Yukihiko, H.3
Saigo, K.4
-
45
-
-
0037071211
-
-
(b) Brummond, K. M.; Sill, P. C.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43. 3735.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 3735
-
-
Brummond, K.M.1
Sill, P.C.2
Rickards, B.3
Geib, S.J.4
-
46
-
-
2442551867
-
-
and references cited therein
-
(c) Chouraqui, G.; Petit, M.; Aubert, C.; Malacria, M. Org. Lett. 2004, 6, 1519 and references cited therein.
-
(2004)
Org. Lett.
, vol.6
, pp. 1519
-
-
Chouraqui, G.1
Petit, M.2
Aubert, C.3
Malacria, M.4
-
47
-
-
0037011303
-
-
Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4550
-
-
Wender, P.A.1
Williams, T.J.2
-
49
-
-
0037879286
-
-
(b) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 1734
-
-
Evans, P.A.1
Cui, J.2
Buffone, G.P.3
-
50
-
-
37049079386
-
-
For pioneering work on the rhodium-catalyzed mtermolecular [2+2+2] carbocylization using tethered 1,6-diynes and 1,6-enynes, see: (a) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 1357
-
-
Grigg, R.1
Scott, R.2
Stevenson, P.3
-
51
-
-
37049067977
-
-
(b) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1365.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 1365
-
-
Grigg, R.1
Scott, R.2
Stevenson, P.3
-
52
-
-
0000830218
-
-
For some recent examples of intermolecular rhodium-catalyzed [2+2+2] carbocyclizations of tethered 1,6-diynes, see: (a) McDonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 6605
-
-
McDonald, F.E.1
Zhu, H.Y.H.2
Holmquist, C.R.3
-
53
-
-
0033549728
-
-
(b) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2426
-
-
Witulski, B.1
Stengel, T.2
-
54
-
-
0038006281
-
-
(c) Nishiyama, H.; Niwa, E.; Inoue, T.; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572.
-
(2002)
Organometallics
, vol.21
, pp. 2572
-
-
Nishiyama, H.1
Niwa, E.2
Inoue, T.3
Ishima, Y.4
Aoki, K.5
-
55
-
-
0037527845
-
-
and pertinent references cited therein
-
(d) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784 and pertinent references cited therein.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 7784
-
-
Kinoshita, H.1
Shinokubo, H.2
Oshima, K.3
-
56
-
-
0035817287
-
-
For a recent example of a rhodium-catalyzed [2+2+2] dimerization of 1,6-enynes, see: Oh, C. H.; Sung, H. R.; Jung, S. H.; Lim, Y. M. Tetrahedron Lett. 2001, 42, 5493.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 5493
-
-
Oh, C.H.1
Sung, H.R.2
Jung, S.H.3
Lim, Y.M.4
-
57
-
-
33845282237
-
-
For examples of an intermolecular metal-catalyzed [2+2+2] carbocyclization with various 1,6-enynes using symmetrical alkynes, see: (a) Pd: Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1987, 109, 4753.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 4753
-
-
Trost, B.M.1
Tanoury, G.J.2
-
58
-
-
18844439402
-
-
(b) Ir: Kezuka, S.; Okado, T.; Niou, E.; Takeuchi, R. Org. Lett. 2005, 7, 1711.
-
(2005)
Org. Lett.
, vol.7
, pp. 1711
-
-
Kezuka, S.1
Okado, T.2
Niou, E.3
Takeuchi, R.4
-
59
-
-
0001442058
-
-
(a) Ohshita, J.; Furumori, K.; Matsuguchi, A.; Ishikawa, M. J. Org. Chem. 1990, 55, 3277.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 3277
-
-
Ohshita, J.1
Furumori, K.2
Matsuguchi, A.3
Ishikawa, M.4
-
60
-
-
0000130663
-
-
(b) Field, L. D.; Ward, A. J.; Turner, P. Aust. J. Chem., 1999, 52, 1085.
-
(1999)
Aust. J. Chem.
, vol.52
, pp. 1085
-
-
Field, L.D.1
Ward, A.J.2
Turner, P.3
-
61
-
-
23944468274
-
-
Evans, P. A.; Sawyer, J. R.; Lai, K. W.; Huffman, J. C. Chem. Commun. 2005, 3971.
-
(2005)
Chem. Commun.
, pp. 3971
-
-
Evans, P.A.1
Sawyer, J.R.2
Lai, K.W.3
Huffman, J.C.4
-
62
-
-
0035930039
-
-
For a trans-hydrometalation with rhodium, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 11492
-
-
Tanaka, K.1
Fu, G.C.2
-
63
-
-
0037012745
-
-
(b) Tanaka, K.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1607.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 1607
-
-
Tanaka, K.1
Fu, G.C.2
-
64
-
-
0010543931
-
-
For an example of a intermolecular cobalt-mediated [2+2+2] carbocyclization with various 1,6-enynes using an unsymmetrical alkyne, see: Chang, C.-A.; King, Jr., J. A.; Vollhardt, K. P. C. J. Chem. Soc., Chem. Commun. 1981, 53.
-
(1981)
J. Chem. Soc., Chem. Commun.
, pp. 53
-
-
Chang, C.-A.1
King Jr., J.A.2
Vollhardt, K.P.C.3
-
65
-
-
0346780615
-
-
For an example of complementary regiochemistry in metallacycle formation, see: Tanaka, K.; Shriasaka, K. Org. Lett. 2003, 5, 4697.
-
(2003)
Org. Lett.
, vol.5
, pp. 4697
-
-
Tanaka, K.1
Shriasaka, K.2
-
66
-
-
24744435554
-
-
Evans, P. A.; Lai, K. W.; Sawyer, J. R. J. Am. Chem. Soc. 2005, 127, 12466.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 12466
-
-
Evans, P.A.1
Lai, K.W.2
Sawyer, J.R.3
-
67
-
-
19044372134
-
-
and pertinent references cited therein
-
For excellent review on the development of chiral bisphosphine ligands, see: Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405 and pertinent references cited therein.
-
(2005)
Tetrahedron
, vol.61
, pp. 5405
-
-
Shimizu, H.1
Nagasaki, I.2
Saito, T.3
-
68
-
-
0347761350
-
-
(a) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidai, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem. Int. Ed. 2004, 43, 320.
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 320
-
-
Jeulin, S.1
Duprat De Paule, S.2
Ratovelomanana-Vidai, V.3
Genêt, J.-P.4
Champion, N.5
Dellis, P.6
-
69
-
-
0034703752
-
-
(a) Pai, C.-C.; Lin, C.-W.; Lin, C.-C.; Chen, C.-C.; Chan, A. S. C.; Wong, W. T. J. Am. Chem. Soc. 2000, 122, 11513.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 11513
-
-
Pai, C.-C.1
Lin, C.-W.2
Lin, C.-C.3
Chen, C.-C.4
Chan, A.S.C.5
Wong, W.T.6
-
70
-
-
0036828018
-
-
(b) Wu, J.; Chen, H.; Kwok, W.; Guo, R.; Zhou, Z.; Yeung, C.; Chan, A. S. C. J. Org. Chem. 2002, 67, 7908.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 7908
-
-
Wu, J.1
Chen, H.2
Kwok, W.3
Guo, R.4
Zhou, Z.5
Yeung, C.6
Chan, A.S.C.7
-
71
-
-
0035905575
-
-
For recent reviews on the enantioselective construction of quaternary carbon stereocenters, see: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 4591
-
-
Christoffers, J.1
Mann, A.2
-
72
-
-
0344064789
-
-
and pertinent references cited therein
-
(b) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105 and pertinent references cited therein.
-
(2003)
Tetrahedron
, vol.59
, pp. 10105
-
-
Denissova, I.1
Barriault, L.2
|