-
4
-
-
0000213863
-
-
(Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim
-
d) N. Jeong, in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, p. 560;
-
(1998)
Transition Metals for Organic Synthesis
, pp. 560
-
-
Jeong, N.1
-
8
-
-
0001136410
-
-
(Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Elsevier, New York
-
g) N. E. Schore, in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703;
-
(1995)
Comprehensive Organometallic Chemistry II, Vol. 12
, vol.12
, pp. 703
-
-
Schore, N.E.1
-
10
-
-
0001334715
-
-
(Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
-
i) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1037;
-
(1991)
Comprehensive Organic Synthesis, Vol. 5
, vol.5
, pp. 1037
-
-
Schore, N.E.1
-
16
-
-
0028827127
-
-
d) T. J. Jamison, S. Simbayati, L. A. Paquette, S. Borrelly, J. Org. Chem. 1995, 60, 6912;
-
(1995)
J. Org. Chem.
, vol.60
, pp. 6912
-
-
Jamison, T.J.1
Simbayati, S.2
Paquette, L.A.3
Borrelly, S.4
-
17
-
-
0030474812
-
-
e) J. Castro, A. Moyano, M. A. Pericàs, A. Riera, A. E. Greene, A. Álvarez-Larena, J. F. Piniella, J. Org. Chem. 1996, 61, 9016;
-
(1996)
J. Org. Chem.
, vol.61
, pp. 9016
-
-
Castro, J.1
Moyano, A.2
Pericàs, M.A.3
Riera, A.4
Greene, A.E.5
Álvarez-Larena, A.6
Piniella, J.F.7
-
18
-
-
0030790172
-
-
f) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4851
-
-
Tormo, J.1
Moyano, A.2
Pericàs, M.A.3
Riera, A.4
-
19
-
-
0030991958
-
-
g) T. J. Jamison, S. Simbayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1997, 119, 4353;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4353
-
-
Jamison, T.J.1
Simbayati, S.2
Crowe, W.E.3
Schreiber, S.L.4
-
20
-
-
0032476127
-
-
h) B. Alcaide, C. Polanco, M. A. Sierra, J. Org. Chem. 1998, 63, 6786;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6786
-
-
Alcaide, B.1
Polanco, C.2
Sierra, M.A.3
-
21
-
-
0000030614
-
-
i) B. A. Kowalczyk, T. C. Smith, W. G. Dauben, J. Org. Chem. 1998, 63, 1379;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 1379
-
-
Kowalczyk, B.A.1
Smith, T.C.2
Dauben, W.G.3
-
23
-
-
0033524683
-
-
k) M. M. Bruendl, S. G. Van Ornum, T-M. Chang, J. M. Cook, Tetrahedron Lett. 1999, 40, 1113;
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 1113
-
-
Bruendl, M.M.1
Van Ornum, S.G.2
Chang, T.-M.3
Cook, J.M.4
-
25
-
-
0034616407
-
-
m) S. G. Van Ornun, M. M. Bruendl, H. Cao, M. Reddy, D. S. Grubisha, D. W. Bennett, J. M. Cook, J. Org. Chem. 2000, 65, 1957.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 1957
-
-
Van Ornun, S.G.1
Bruendl, M.M.2
Cao, H.3
Reddy, M.4
Grubisha, D.S.5
Bennett, D.W.6
Cook, J.M.7
-
27
-
-
0023222798
-
-
b) P. Magnus, L. M. Principe, M. J. Slater, J. Org. Chem. 1987, 52, 1483;
-
(1987)
J. Org. Chem.
, vol.52
, pp. 1483
-
-
Magnus, P.1
Principe, L.M.2
Slater, M.J.3
-
29
-
-
33745353321
-
-
d) P. Magnus, C. Exon, P. Albaugh-Robertson, Tetrahedron 1985, 41, 5861.
-
(1985)
Tetrahedron
, vol.41
, pp. 5861
-
-
Magnus, P.1
Exon, C.2
Albaugh-Robertson, P.3
-
30
-
-
0034613217
-
-
For other examples of exo selectivity in PK cyclizations of enynes substituted at allylic or propargylic positions, see: a) C. Mukai, H. Sonobe, J. S. Kim, M. Hanoka, J. Org. Chem. 2000, 65, 6654;
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6654
-
-
Mukai, C.1
Sonobe, H.2
Kim, J.S.3
Hanoka, M.4
-
31
-
-
33748636502
-
-
b) C. Mukai, J. S. Kim, M. Uchiyama, S. Sakamoto, M. Hanoka, J. Chem. Soc. Perkin Trans. 1 1998, 2903;
-
(1998)
J. Chem. Soc. Perkin Trans. 1
, pp. 2903
-
-
Mukai, C.1
Kim, J.S.2
Uchiyama, M.3
Sakamoto, S.4
Hanoka, M.5
-
32
-
-
0029115708
-
-
c) C. Mukai, M. Uchiyama, S. Sakamoto, M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761;
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 5761
-
-
Mukai, C.1
Uchiyama, M.2
Sakamoto, S.3
Hanaoka, M.4
-
33
-
-
0001069332
-
-
d) N. Jeong, S. Hwang, Y. Lee, Y. K. Chung, J. Am. Chem. Soc. 1994, 116, 3159;
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 3159
-
-
Jeong, N.1
Hwang, S.2
Lee, Y.3
Chung, Y.K.4
-
34
-
-
0000795340
-
-
e) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics, 1993, 12, 220;
-
(1993)
Organometallics
, vol.12
, pp. 220
-
-
Chung, Y.K.1
Lee, B.Y.2
Jeong, N.3
Hudecek, M.4
Pauson, P.L.5
-
35
-
-
0027299437
-
-
f) N. Jeong, B. Y. Lee, S. M. Lee, Y. K. Chung, S.-G. Lee, Tetrahedron Lett. 1993, 34, 4023;
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 4023
-
-
Jeong, N.1
Lee, B.Y.2
Lee, S.M.3
Chung, Y.K.4
Lee, S.-G.5
-
36
-
-
0002814146
-
-
g) S. Yoo, S. H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3425;
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 3425
-
-
Yoo, S.1
Lee, S.H.2
Jeong, N.3
Cho, I.4
-
38
-
-
0025859459
-
-
i) N. Jeong, S. Yoo, S. J. Lee, S. H. Lee, Y. K. Chung, Tetrahedron Lett. 1991, 32, 2137;
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 2137
-
-
Jeong, N.1
Yoo, S.2
Lee, S.J.3
Lee, S.H.4
Chung, Y.K.5
-
40
-
-
0001191177
-
-
It has been known since the pioneering studies of Pauson and Khand that the reaction of alkyne dicobalt hexacarbonyl complexes with alkenes bearing electron-withdrawing groups (such as ethyl acrylate, acrylonitrile, methylvinylketone or divinyldisulfone) resulted predominantly in 1,3-dienes instead of the corresponding cyclopentenones. This behavior has been explained by the postulation that in these cases the cobaltacycle intermediate undergoes β-H elimination and formation of a conjugated alkene more rapidly than it does carbonyl insertion. See, for example: a) W. A. Smit, A. S. Gybin, A. S. Shashkov, Y. T. Strychkov, L. G. Kizmina, G. S. Mikaelian, R. Caple, E. D. Swanson, Tetrahedron Lett. 1986, 27, 1241;
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 1241
-
-
Smit, W.A.1
Gybin, A.S.2
Shashkov, A.S.3
Strychkov, Y.T.4
Kizmina, L.G.5
Mikaelian, G.S.6
Caple, R.7
Swanson, E.D.8
-
44
-
-
0025884430
-
-
a) A. L. Veretenov, W. A. Smit, L. G. Vorontsova, M. G. Kurella, R. Caple, A. S. Gibin, Tetrahedron Lett. 1991, 32, 2109;
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 2109
-
-
Veretenov, A.L.1
Smit, W.A.2
Vorontsova, L.G.3
Kurella, M.G.4
Caple, R.5
Gibin, A.S.6
-
46
-
-
0033165960
-
-
M. Ahmar, F. Antras, B. Cazes, Tetrahedron Lett. 1999, 40, 5503.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 5503
-
-
Ahmar, M.1
Antras, F.2
Cazes, B.3
-
48
-
-
47249110665
-
-
For recent references, see: a) J. deVicente, R. Gómez Arrayás, J. Cañada, J. C. Carretero, Synlett 2000, 53;
-
(2000)
Synlett
, pp. 53
-
-
DeVicente, J.1
Gómez Arrayás, R.2
Cañada, J.3
Carretero, J.C.4
-
49
-
-
0033551798
-
-
b) J. deVicente, R. Gómez Arrayás, J. C. Carretero, Tetrahedron Lett. 1999, 40, 6083;
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 6083
-
-
DeVicente, J.1
Gómez Arrayás, R.2
Carretero, J.C.3
-
51
-
-
0344117715
-
-
To the best of our knowledge, the only reported examples of endo selectivity in a PK reaction of an allylic substituted enyne concerns some specific 3,4-disubstituted enynes, see: a) C. Mukai, J. S. Kim, H. Sonobe, M. Hanaoka, J. Org. Chem. 1999, 64, 6822;
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6822
-
-
Mukai, C.1
Kim, J.S.2
Sonobe, H.3
Hanaoka, M.4
-
52
-
-
0028330334
-
-
b) J. A. Casalnuovo, R. W. Scott, E. A. Harwood, N. E. Schore, 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
-
53
-
-
0000956077
-
-
Previous communication: J. Adrio, M. Rodríguez Rivero, J. C. Carretero, Angew. Chem. 2000, 112, 3028;
-
(2000)
Angew. Chem.
, vol.112
, pp. 3028
-
-
Adrio, J.1
Rodríguez Rivero, M.2
Carretero, J.C.3
-
55
-
-
33751500117
-
-
For the synthesis of γ-hydroxy-α,β-unsaturated sulfones by condensation of aldehydes with sulfinyl sulfonyl methanes, see: a) B. M. Trost, T. A. Greese, J. Org. Chem. 1991, 56, 3189;
-
(1991)
J. Org. Chem.
, vol.56
, pp. 3189
-
-
Trost, B.M.1
Greese, T.A.2
-
57
-
-
0003463148
-
-
Wiley, New York
-
T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999.
-
(1999)
Protective Groups in Organic Synthesis, 3rd Ed.
-
-
Greene, T.W.1
Wuts, P.G.M.2
-
58
-
-
20444497278
-
-
note
-
Crystallographic data (excluding structure factors) for the structure endo-9c reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-141942. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam. ac.uk)..
-
-
-
-
59
-
-
0000354667
-
-
2, RT; j) nBuLi, THF, 0°C; k) 5M HCl, MeOH, RT; l) NaOH, propargyl bromide, RT. See also: a) W. Oppolzer, J. Z. Xu, C. Stone, Helv. Chim. Acta 1991, 74, 465;
-
(1991)
Helv. Chim. Acta
, vol.74
, pp. 465
-
-
Oppolzer, W.1
Xu, J.Z.2
Stone, C.3
-
60
-
-
0002804030
-
-
b) E. Hernández, A. Galan, C. Rovira, J. Veciana, Synthesis 1992, 465.
-
(1992)
Synthesis
, pp. 465
-
-
Hernández, E.1
Galan, A.2
Rovira, C.3
Veciana, J.4
-
61
-
-
0040830739
-
-
The combination of TMANO and molecular sieves has recently been reported as an efficient promoter in PK reactions, see: a) L. Pérez-Serrano, L. Casarrubios, G. Domínguez, J. Pérez-Castells, Org. Lett. 1999, 1, 1187;
-
(1999)
Org. Lett.
, vol.1
, pp. 1187
-
-
Pérez-Serrano, L.1
Casarrubios, L.2
Domínguez, G.3
Pérez-Castells, J.4
-
62
-
-
0034595752
-
-
b) L. Pérez-Serrano, J. Blanco-Urgoiti, L. Casarrubios, G. Domínguez, J. Pérez-Castells, J. Org. Chem. 2000, 65, 3513.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3513
-
-
Pérez-Serrano, L.1
Blanco-Urgoiti, J.2
Casarrubios, L.3
Domínguez, G.4
Pérez-Castells, J.5
-
63
-
-
0001054580
-
-
R. A. Holton, D. J. Crouse, A. D. Williams, R. M. Kennedy, J. Org. Chem. 1987, 52, 2317.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 2317
-
-
Holton, R.A.1
Crouse, D.J.2
Williams, A.D.3
Kennedy, R.M.4
-
66
-
-
0025068753
-
-
For another method for the enantioselective preparation of γ-hydroxy-α,β-unsaturated sulfones, see: E. J. Corey, R. K. Bakshi, Tetrahedron Lett. 1990, 31, 611.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 611
-
-
Corey, E.J.1
Bakshi, R.K.2
-
67
-
-
0033612115
-
-
For representative references, see, for example: a) P. M. Breczinski, A. Stumpf, H. Hope, M. E. Krafft, J. A. Casalnuovo, N. E. Schore, Tetrahedron 1999, 55, 6797;
-
(1999)
Tetrahedron
, vol.55
, pp. 6797
-
-
Breczinski, P.M.1
Stumpf, A.2
Hope, H.3
Krafft, M.E.4
Casalnuovo, J.A.5
Schore, N.E.6
-
68
-
-
0029052457
-
-
b) J. Castro, A. Moyano, M. A. Pericàs, A. Riera, Tetrahedron 1995, 51, 6541.
-
(1995)
Tetrahedron
, vol.51
, pp. 6541
-
-
Castro, J.1
Moyano, A.2
Pericàs, M.A.3
Riera, A.4
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