-
2
-
-
0017038349
-
-
For selected examples for seven-membered heterocycles, see: (a) Duong, T.; Prager, R. H.; Tippett, J. M.; Ward, A. D.; Kerr, D. I. Aus. J. Chem. 1976, 29, 2667-2682.
-
(1976)
Aus. J. Chem.
, vol.29
, pp. 2667-2682
-
-
Duong, T.1
Prager, R.H.2
Tippett, J.M.3
Ward, A.D.4
Kerr, D.I.5
-
3
-
-
0028146990
-
-
(b) Boros, C.; Hamilton, S. M.; Katz, B.; Kulanthaivel, P. J. Antibiot. 1994, 47, 1010-1016.
-
(1994)
J. Antibiot.
, vol.47
, pp. 1010-1016
-
-
Boros, C.1
Hamilton, S.M.2
Katz, B.3
Kulanthaivel, P.4
-
4
-
-
0028104107
-
-
(c) Ishihara, Y.; Hirai, K.; Miyamoto, M.; Goto, G. J. Med. Chem. 1994, 37, 2292-2299.
-
(1994)
J. Med. Chem.
, vol.37
, pp. 2292-2299
-
-
Ishihara, Y.1
Hirai, K.2
Miyamoto, M.3
Goto, G.4
-
5
-
-
0029840739
-
-
(d) Morrís-Varas, F.; Qian, X.-H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 33, 7647-7652.
-
(1996)
J. Am. Chem. Soc.
, vol.33
, pp. 7647-7652
-
-
Morrís-Varas, F.1
Qian, X.-H.2
Wong, C.-H.3
-
6
-
-
0029795609
-
-
(e) Grunewald, G. L.; Dahanukar, V. H.; Ching, P.; Criscione, K. R. J. Med. Chem. 1996, 39, 3539-3546.
-
(1996)
J. Med. Chem.
, vol.39
, pp. 3539-3546
-
-
Grunewald, G.L.1
Dahanukar, V.H.2
Ching, P.3
Criscione, K.R.4
-
7
-
-
0014785369
-
-
For selected examples for eight-membered heterocycles, see: (a) Basil, B.; Coffee, E. C. J.; Gell, D. L.; Maxwell, D. R.; Sheffield, D. J.; Wooldridge, K. R. H. J. Med. Chem. 1970, 13, 403-406.
-
(1970)
J. Med. Chem.
, vol.13
, pp. 403-406
-
-
Basil, B.1
Coffee, E.C.J.2
Gell, D.L.3
Maxwell, D.R.4
Sheffield, D.J.5
Wooldridge, K.R.H.6
-
8
-
-
0018643963
-
-
(b) Klayman, D. L.; Scovill, J. P.; Bartosevich, J. F.; Mason, C. J. J. Med. Chem. 1979, 22, 1367-1373.
-
(1979)
J. Med. Chem.
, vol.22
, pp. 1367-1373
-
-
Klayman, D.L.1
Scovill, J.P.2
Bartosevich, J.F.3
Mason, C.J.4
-
9
-
-
0032557197
-
-
(c) Vedejs, E.; Galante, R. J.; Goekjian, P. G. J. Am. Chem. Soc. 1998, 120, 3613-3622.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 3613-3622
-
-
Vedejs, E.1
Galante, R.J.2
Goekjian, P.G.3
-
10
-
-
0037062886
-
-
(d) Ma, D.; Tang, G.; Kozikowski, A. P. Org. Lett. 2002, 4, 2377-2380.
-
(2002)
Org. Lett.
, vol.4
, pp. 2377-2380
-
-
Ma, D.1
Tang, G.2
Kozikowski, A.P.3
-
11
-
-
0141746194
-
-
and references therein
-
(e) Stærk, D.; Witt, M.; Oketch-Rabah, H. A.; Jaroszewski, J. W. Org. Lett. 2003, 5, 2793-2796 and references therein.
-
(2003)
Org. Lett.
, vol.5
, pp. 2793-2796
-
-
Stærk, D.1
Witt, M.2
Oketch-Rabah, H.A.3
Jaroszewski, J.W.4
-
14
-
-
0001647405
-
-
(c) Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 2108-2109
-
-
Miller, S.J.1
Kim, S.-H.2
Chen, Z.-R.3
Grubbs, R.H.4
-
15
-
-
17544377767
-
-
(d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 4291-4298
-
-
Visser, M.S.1
Heron, N.M.2
Didiuk, M.T.3
Sagal, J.F.4
Hoveyda, A.H.5
-
17
-
-
0033606861
-
-
(f) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615-617.
-
(1999)
Org. Lett.
, vol.1
, pp. 615-617
-
-
Cook, G.R.1
Shanker, P.S.2
Peterson, S.L.3
-
18
-
-
0001603182
-
-
(g) Mori, M.; Kitamura, T.; Sakakibara, N.; Sato, Y. Org. Lett. 2000, 2, 543-545.
-
(2000)
Org. Lett.
, vol.2
, pp. 543-545
-
-
Mori, M.1
Kitamura, T.2
Sakakibara, N.3
Sato, Y.4
-
19
-
-
0035914638
-
-
(h) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811-4820.
-
(2001)
Chem. Eur. J.
, vol.7
, pp. 4811-4820
-
-
Fürstner, A.1
Guth, O.2
Düffels, A.3
Seidel, G.4
Liebl, M.5
Gabor, B.6
Mynott, R.7
-
20
-
-
0037134887
-
-
(i) Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991-6997.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 6991-6997
-
-
Dolman, S.J.1
Sattely, E.S.2
Hoveyda, A.H.3
Schrock, R.R.4
-
21
-
-
1542451475
-
-
For other recent synthesis of medium-ring heterocycles, see: (a) Evans, P. A.; Holmes, A. B.; Russel, K. Tetrahedron: Asymmetry 1990, 1, 593-596.
-
(1990)
Tetrahedron: Asymmetry
, vol.1
, pp. 593-596
-
-
Evans, P.A.1
Holmes, A.B.2
Russel, K.3
-
22
-
-
37049071932
-
-
(b) Kitano, T.; Shirai, N.; Motoi, M.; Sato, Y. J. Chem. Soc., Perkin Trans. 1 1992, 2851-2854.
-
(1992)
J. Chem. Soc., Perkin Trans. 1
, pp. 2851-2854
-
-
Kitano, T.1
Shirai, N.2
Motoi, M.3
Sato, Y.4
-
23
-
-
37049066338
-
-
(c) Crombie, L.; Haigh, D.; Jones, R. C. F.; Mat-Zin, A. R. J. Chem. Soc., Perkin Trans. 1 1993, 2047-2054.
-
(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 2047-2054
-
-
Crombie, L.1
Haigh, D.2
Jones, R.C.F.3
Mat-Zin, A.R.4
-
25
-
-
0029930972
-
-
(e) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165-2168.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 2165-2168
-
-
Wright, D.L.1
Weekly, R.M.2
Groff, R.3
McMills, M.C.4
-
26
-
-
0033166401
-
-
(f) Bergmann, D. J.; Campi, E. M.; Jackson, W. R.; Patti, A. F.; Saylik, D. Tetrahedron Lett. 1999, 40, 5597-5600.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 5597-5600
-
-
Bergmann, D.J.1
Campi, E.M.2
Jackson, W.R.3
Patti, A.F.4
Saylik, D.5
-
28
-
-
0033525092
-
-
(h) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1074-1076
-
-
Zhang, J.1
Jacobson, A.2
Rusche, J.R.3
Herlihy, W.4
-
29
-
-
0034639462
-
-
(i) Monovich, L. G.; Huérou. Y. L.; Rönn. M.; Molander, G. A. J. Am. Chem. Soc. 2000, 122, 52-57.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 52-57
-
-
Monovich, L.G.1
Huérou, Y.L.2
Rönn, M.3
Molander, G.A.4
-
30
-
-
0034693109
-
-
(j) Räcker, R.; Döring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932-6939.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6932-6939
-
-
Räcker, R.1
Döring, K.2
Reiser, O.3
-
31
-
-
0035936757
-
-
(k) Meyers, A. I.; Downing, S. V.; Weiser, M. J. J. Org. Chem. 2001, 66, 1413-1419.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 1413-1419
-
-
Meyers, A.I.1
Downing, S.V.2
Weiser, M.J.3
-
32
-
-
0035932581
-
-
(l) Donohoe, T. J.; Raoof, A.; Linney, I. D.; Helliwell, M. Org. Lett. 2001, 3, 861-864.
-
(2001)
Org. Lett.
, vol.3
, pp. 861-864
-
-
Donohoe, T.J.1
Raoof, A.2
Linney, I.D.3
Helliwell, M.4
-
33
-
-
0035922363
-
-
(m) Iradier, F.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2001, 3, 2957-2960.
-
(2001)
Org. Lett.
, vol.3
, pp. 2957-2960
-
-
Iradier, F.1
Arrayás, R.G.2
Carretero, J.C.3
-
34
-
-
0035939470
-
-
(n) Tempest, P.; Ma, V.; Kelly, M. G.; Jones, W.; Hulme, C. Tetrahedron Lett. 2001, 42, 4963-4968.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 4963-4968
-
-
Tempest, P.1
Ma, V.2
Kelly, M.G.3
Jones, W.4
Hulme, C.5
-
36
-
-
0037062886
-
-
See also ref 3c
-
(p) Ma, D.; Tang, G.; Kozikowski, A. P. Org. Lett. 2002, 4, 2377-2380. See also ref 3c.
-
(2002)
Org. Lett.
, vol.4
, pp. 2377-2380
-
-
Ma, D.1
Tang, G.2
Kozikowski, A.P.3
-
38
-
-
0000035726
-
-
(b) Caporusso, A. M.; Polizzi, C.; Lardicci, L. Tetrahedron Lett. 1987, 28, 6073-6076.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 6073-6076
-
-
Caporusso, A.M.1
Polizzi, C.2
Lardicci, L.3
-
39
-
-
0030036926
-
-
(c) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4870-4871
-
-
D'Aniello, F.1
Mann, A.2
Taddei, M.3
-
40
-
-
0031037358
-
-
(d) D'Aniello, F.; Mann, A.; Schoenfelder, A.; Taddei, M. Tetrahedron 1997, 53, 1447-1456.
-
(1997)
Tetrahedron
, vol.53
, pp. 1447-1456
-
-
D'Aniello, F.1
Mann, A.2
Schoenfelder, A.3
Taddei, M.4
-
41
-
-
0033605184
-
-
(e) Bernard, N.; Chemla, F.; Normant, J. F. Tetrahedron Lett. 1999, 40, 1649-1652.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 1649-1652
-
-
Bernard, N.1
Chemla, F.2
Normant, J.F.3
-
43
-
-
0034685223
-
-
(g) Caporusso, A. M.; Filippi, S.; Barontini, F.; Salvadori, P. Tetrahedron Lett. 2000, 41, 1227-1230.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 1227-1230
-
-
Caporusso, A.M.1
Filippi, S.2
Barontini, F.3
Salvadori, P.4
-
45
-
-
0012114207
-
-
(a) Märkl, G.; Attenberger, P.; Kellner, J. Tetrahedron Lett. 1988, 29, 3651-3654.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 3651-3654
-
-
Märkl, G.1
Attenberger, P.2
Kellner, J.3
-
46
-
-
77954853973
-
-
(b) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257-1259.
-
(1995)
Synlett
, pp. 1257-1259
-
-
Gillmann, T.1
Hülsen, T.2
Massa, W.3
Wocadlo, S.4
-
47
-
-
0033588136
-
-
(c) Saalfrank, R. W.; Haubner, M.; Deutscher, C.; Bauer, W.; Clark, T. J. Org. Chem. 1999, 64, 6166-6168.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6166-6168
-
-
Saalfrank, R.W.1
Haubner, M.2
Deutscher, C.3
Bauer, W.4
Clark, T.5
-
48
-
-
0032830892
-
-
(d) Saalfrank, R. W.; Haubner, M.; Deutscher, C.; Bauer, W. Eur. J. Org. Chem. 1999, 2367-2372.
-
(1999)
Eur. J. Org. Chem.
, pp. 2367-2372
-
-
Saalfrank, R.W.1
Haubner, M.2
Deutscher, C.3
Bauer, W.4
-
50
-
-
0242576780
-
-
(b) Ma, S.; Yu, S.; Yin, S. J. Org. Chem. 2003, 68, 8996-9002.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 8996-9002
-
-
Ma, S.1
Yu, S.2
Yin, S.3
-
51
-
-
0035954878
-
-
(a) Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2001, 3, 2269-2271.
-
(2001)
Org. Lett.
, vol.3
, pp. 2269-2271
-
-
Ohno, H.1
Hamaguchi, H.2
Tanaka, T.3
-
52
-
-
0347928822
-
-
(b) Ohno, H.; Ando, K.; Hamaguchi, H.; Takeoka, Y.; Tanaka, T. J. Am. Chem. Soc. 2002, 124, 15255-15266.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 15255-15266
-
-
Ohno, H.1
Ando, K.2
Hamaguchi, H.3
Takeoka, Y.4
Tanaka, T.5
-
53
-
-
0001549837
-
-
(a) Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196-2198.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 2196-2198
-
-
Tsuji, J.1
Watanabe, H.2
Minami, I.3
Shimizu, I.4
-
54
-
-
33751055792
-
-
For an excellent review, see: (b) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. 1995, 34, 2589-2612.
-
(1995)
Angew. Chem., Int. Ed.
, vol.34
, pp. 2589-2612
-
-
Tsuji, J.1
Mandai, T.2
-
56
-
-
0035793267
-
-
(d) Yoshida, M.; Ihara, M. Angew. Chem., Int. Ed. 2001, 40, 616-619.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 616-619
-
-
Yoshida, M.1
Ihara, M.2
-
57
-
-
0035812738
-
-
(e) Labrosse, J.-R.; Lhoste, P.; Sinou, D. J. Org. Chem. 2001, 66, 6634-6642.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 6634-6642
-
-
Labrosse, J.-R.1
Lhoste, P.2
Sinou, D.3
-
62
-
-
0141632683
-
-
(j) Yoshida, M.; Fujita, M.; Ihara, M. Org. Lett. 2003, 5, 3325-3327.
-
(2003)
Org. Lett.
, vol.5
, pp. 3325-3327
-
-
Yoshida, M.1
Fujita, M.2
Ihara, M.3
-
64
-
-
0037901449
-
-
(b) Okawara, T.; Ehara, S.; Takenaka, A.; Hiwatashi, T.; Furukawa, M. Heterocycles 1995, 41, 1709-1714.
-
(1995)
Heterocycles
, vol.41
, pp. 1709-1714
-
-
Okawara, T.1
Ehara, S.2
Takenaka, A.3
Hiwatashi, T.4
Furukawa, M.5
-
66
-
-
0030800450
-
-
(d) Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. Angew. Chem., Int. Ed. 1997, 36, 1750-1753.
-
(1997)
Angew. Chem., Int. Ed.
, vol.36
, pp. 1750-1753
-
-
Trost, B.M.1
Michellys, P.-Y.2
Gerusz, V.J.3
-
67
-
-
0000344904
-
-
(e) Larock, R. C.; Tu, C.; Pace, P. J. Org. Chem. 1998, 63, 6859-6866.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6859-6866
-
-
Larock, R.C.1
Tu, C.2
Pace, P.3
-
68
-
-
0038076018
-
-
For preliminary communications, see: (a) Ohno, H.; Hamaguchi, H.; Ohata, M.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 1749-1753.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 1749-1753
-
-
Ohno, H.1
Hamaguchi, H.2
Ohata, M.3
Tanaka, T.4
-
69
-
-
0346392203
-
-
(b) Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. Heterocycles 2003, 61, 65-68.
-
(2003)
Heterocycles
, vol.61
, pp. 65-68
-
-
Ohno, H.1
Hamaguchi, H.2
Ohata, M.3
Kosaka, S.4
Tanaka, T.5
-
70
-
-
3242729802
-
-
note
-
The bromoallenes 13b-d were synthesized according to the reported procedure.9 For synthesis of the bromoallene 13a, see the Supporting Information.
-
-
-
-
71
-
-
0028069277
-
-
N-Boc sulfonamides, a useful nitrogen nucleophile in the Mitsunobu reaction, can be readily prepared by the reaction of sulfonamides with di-(tert-butyl) dicarbonate catalyzed by 4-(dimethylamino)pyridine: Neustadt, B. R. Tetrahedron Lett. 1994, 35, 379-380.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 379-380
-
-
Neustadt, B.R.1
-
72
-
-
3242660348
-
-
note
-
Structure of 24b was confirmed by NOE analysis. Irradiation of the signal of 6-H in 1,4-oxazepine 24b led to NOE enhancement of the signal of 5-H and 1′-H (12.3% for 5-H and 7.2% for 1′-H). (Diagram presented)
-
-
-
-
73
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3242703593
-
-
note
-
For synthesis of bromoallenes 15e and 17e, see the Supporting Information.
-
-
-
-
74
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3242691894
-
-
note
-
The cis-configuration of the eight-membered ring 26 was determined by NOE analysis. For example, in the case of 1,5-oxazocine 26b, NOE was observed between [6-H and 7-H (9.6%)] and [7-H and 1′-H (5.2%)]. (Diagram presented)
-
-
-
-
75
-
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3242720891
-
-
note
-
The (S,aR)-bromoallenes 28 and 29 were synthesized by the identical procedure shown in Scheme 4 from known allenes.9 For details, see the Supporting Information.
-
-
-
-
76
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3242722668
-
-
note
-
Structure of 32 was confirmed by NOE analysis as shown below. (Diagram presented)
-
-
-
-
77
-
-
0000120488
-
-
Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 27, 2099-2102.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 2099-2102
-
-
Weinreb, S.M.1
Demko, D.M.2
Lessen, T.A.3
-
79
-
-
0001319573
-
-
(b) Elsevier, C. J.; Meijer, J.; Tadema, G-, Stehouwer, P. M.; Bos, H. J. T.; Vermeer, P. J. Org. Chem. 1982, 47, 2194-2196.
-
(1982)
J. Org. Chem.
, vol.47
, pp. 2194-2196
-
-
Elsevier, C.J.1
Meijer, J.2
Tadema, G.3
Stehouwer, P.M.4
Bos, H.J.T.5
Vermeer, P.6
-
81
-
-
0019170568
-
-
(b) Kaiser, C.; Ali, F. E.; Bondinell, W. E.; Brenner, M.; Holden, K. G.; Ku, T. W.; Oh, H.-J.; Ross, S. T.; Yim, N. C. F.; Zirkle, C. L.; Hahn, R. A.; Sarau, H. M.; Setler, P. E.; Wardell, J. R., Jr. J. Med. Chem. 1980, 23, 975-976.
-
(1980)
J. Med. Chem.
, vol.23
, pp. 975-976
-
-
Kaiser, C.1
Ali, F.E.2
Bondinell, W.E.3
Brenner, M.4
Holden, K.G.5
Ku, T.W.6
Oh, H.-J.7
Ross, S.T.8
Yim, N.C.F.9
Zirkle, C.L.10
Hahn, R.A.11
Sarau, H.M.12
Setler, P.E.13
Wardell Jr., J.R.14
-
82
-
-
33845283120
-
-
See also refs 2c and 3d
-
(c) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. See also refs 2c and 3d.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 7914-7915
-
-
Flynn, G.A.1
Giroux, E.L.2
Dage, R.C.3
-
83
-
-
0027999360
-
-
Prakash, C.; Saleh, S.; Blair, I. A. Tetrahedron Lett. 1994, 35, 7565-7568.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 7565-7568
-
-
Prakash, C.1
Saleh, S.2
Blair, I.A.3
-
84
-
-
0007412122
-
-
Landor, P. D.; Landor, S. R.; Leighton, P. J. Chem. Soc., Perkin Trans. 1 1975, 1628-1632.
-
(1975)
J. Chem. Soc., Perkin Trans. 1
, pp. 1628-1632
-
-
Landor, P.D.1
Landor, S.R.2
Leighton, P.3
-
85
-
-
33749098217
-
-
Consonni, R.; Croce, P. D.; Ferraccioli, R.; Rosa, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 1809-1814.
-
(1996)
J. Chem. Soc., Perkin Trans. 1
, pp. 1809-1814
-
-
Consonni, R.1
Croce, P.D.2
Ferraccioli, R.3
Rosa, C.L.4
-
87
-
-
3242655876
-
-
note
-
Exposure of the minor product 57 to the cyclization conditions led to complete recovery of 57.
-
-
-
-
88
-
-
3242720890
-
-
note
-
Structure of 64 was confirmed by NOE analysis as shown below. (Diagram presented)
-
-
-
-
89
-
-
3242697375
-
-
note
-
Although formation of benzo-annulated eight-membered ring proceeded in good yields (Table 5, entries 3 and 6), reaction of bromoallene 90 under the same reaction conditions afforded dimethoxylated product 91. Therefore, it is apparent that a substitution which effectively assists the cyclization is essential for the eight-membered ring formation containing one heteroatom. (Diagram presented)
-
-
-
-
90
-
-
3242687436
-
-
note
-
The trans-configuration of 67 was determined by NOE analysis as shown below. (Diagram presented)
-
-
-
-
91
-
-
0002538829
-
-
(a) Ogoshi, S.; Tsutsumi, K.; Nishiguchi, S.; Kurosawa, H. J. Organomet. Chem. 1995, 493, C19-C21.
-
(1995)
J. Organomet. Chem.
, vol.493
-
-
Ogoshi, S.1
Tsutsumi, K.2
Nishiguchi, S.3
Kurosawa, H.4
-
92
-
-
0032481580
-
-
(b) Tsutsumi, K.; Ogoshi, S.; Nishiguchi, S.; Kurosawa, H. J. Am. Chem. Soc. 1998, 120, 1938-1939.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 1938-1939
-
-
Tsutsumi, K.1
Ogoshi, S.2
Nishiguchi, S.3
Kurosawa, H.4
-
93
-
-
0033459584
-
-
(c) Tsutsumi, K.; Kawase, T.; Kakiuchi, K.; Ogoshi, S.; Okada, Y.; Kurosawa, H. Bull. Chem. Soc. Jpn. 1999, 72, 2687-2692.
-
(1999)
Bull. Chem. Soc. Jpn.
, vol.72
, pp. 2687-2692
-
-
Tsutsumi, K.1
Kawase, T.2
Kakiuchi, K.3
Ogoshi, S.4
Okada, Y.5
Kurosawa, H.6
-
95
-
-
0032481404
-
-
See also, ref 10j
-
3- allylpalladium complex: Casey, C. P.; Nash, J. R.; Yi, C. S.; Selmeczy, A. D.; Chung, S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 722-733. See also, ref 10j.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 722-733
-
-
Casey, C.P.1
Nash, J.R.2
Yi, C.S.3
Selmeczy, A.D.4
Chung, S.5
Powell, D.R.6
Hayashi, R.K.7
-
96
-
-
3242737008
-
-
note
-
2 gave the 2-vinylpiperidine 93 in 51% yield along with a trace amount of 59 (ca. 1% yield). From this result, the alternative mechanism through the terminal allene 92 cannot be the major reaction pathway. (Diagram presented)
-
-
-
-
97
-
-
0023805222
-
-
A palladium(II) catalyst induces nucleophilic reaction onto allenes, see: (a) Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 4257-4260.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 4257-4260
-
-
Prasad, J.S.1
Liebeskind, L.S.2
-
98
-
-
33751392574
-
-
(b) Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1992, 57, 6377-6379.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 6377-6379
-
-
Kimura, M.1
Fugami, K.2
Tanaka, S.3
Tamaru, Y.4
-
99
-
-
0030741861
-
-
Hiemstra reported that the cyclization of allenic lactams takes place at the central carbon atom of allene: (c) Karstens, W. F. J.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron Lett. 1997, 38, 6275-6278.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 6275-6278
-
-
Karstens, W.F.J.1
Rutjes, F.P.J.T.2
Hiemstra, H.3
-
100
-
-
0001706911
-
-
(d) Karstens, W. F. J.; Stol, M.; Rutjes, F. P. J. T.; Hiemstra, H. Synlett 1998, 1126-1128.
-
(1998)
Synlett
, pp. 1126-1128
-
-
Karstens, W.F.J.1
Stol, M.2
Rutjes, F.P.J.T.3
Hiemstra, H.4
-
101
-
-
0032560834
-
-
2-Vinylpiperidines were synthesized from amino allenes in the presence of a catalytic amount of a palladium complex under weakly acidic conditions: (e) Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 5421-5424.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 5421-5424
-
-
Meguro, M.1
Yamamoto, Y.2
-
102
-
-
3242700027
-
-
note
-
4.12a
-
-
-
-
103
-
-
0003102896
-
-
See also, refs 31c and 32
-
Baize, M. W.; Blosser, P. W.; Plantevin, V.; Schimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1996, 15, 164-173. See also, refs 31c and 32.
-
(1996)
Organometallics
, vol.15
, pp. 164-173
-
-
Baize, M.W.1
Blosser, P.W.2
Plantevin, V.3
Schimpff, D.G.4
Gallucci, J.C.5
Wojcicki, A.6
-
104
-
-
3242695571
-
-
note
-
For synthesis of the bromoallene 83 bearing two oxygen nucleophiles, see the Supporting Information.
-
-
-
-
105
-
-
3242710766
-
-
note
-
The stereochemistry of the bicyclic product 87 was confirmed by NOE experiment and COSY analysis. (Diagram presented)
-
-
-
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