-
1
-
-
11844288998
-
-
For reviews, see: (a) Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 1, 23-44.
-
(2005)
Eur. J. Org. Chem.
, vol.1
, pp. 23-44
-
-
Hsung, R.P.1
Kurdyumov, A.V.2
Sydorenko, N.3
-
5
-
-
11844292757
-
-
For recent studies in this area, see: (a) Goodenough, K. M.; Moran, W. J.; Raubo, P.; Harrity, J. P. A. J. Org. Chem. 2005, 70, 207.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 207
-
-
Goodenough, K.M.1
Moran, W.J.2
Raubo, P.3
Harrity, J.P.A.4
-
6
-
-
10844243944
-
-
(b) Bose, G.; Nguyen, V. T. H.; Ullah, E.; Lahiri, S.; Görls, H.; Langer, P. J. Org. Chem. 2004, 69, 9128.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 9128
-
-
Bose, G.1
Nguyen, V.T.H.2
Ullah, E.3
Lahiri, S.4
Görls, H.5
Langer, P.6
-
7
-
-
0041696518
-
-
(c) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 6527
-
-
Abelman, M.M.1
Curtis, J.K.2
James, D.R.3
-
8
-
-
0038441546
-
-
(d) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 4286
-
-
Hedley, S.J.1
Moran, W.J.2
Price, D.A.3
Harrity, J.P.A.4
-
9
-
-
0038619436
-
-
(e) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079.
-
(2002)
J. Chin. Chem. Soc.
, vol.49
, pp. 1079
-
-
Chang, M.-Y.1
Lin, J.Y.-C.2
Chen, S.T.3
Chang, N.-C.4
-
10
-
-
0034815578
-
-
(f) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596.
-
(2001)
Synlett
, pp. 1596
-
-
Hedley, S.J.1
Moran, W.J.2
Prenzel, A.H.G.P.3
Price, D.A.4
Harrity, J.P.A.5
-
11
-
-
0035945767
-
-
(g) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209.
-
(2001)
Org. Lett.
, vol.3
, pp. 209
-
-
Davies, I.W.1
Marcoux, J.-F.2
Reider, P.J.3
-
12
-
-
0035847199
-
-
(h) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem., 2001, 66, 251.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 251
-
-
Davies, I.W.1
Taylor, M.2
Marcoux, J.-F.3
Wu, J.4
Dormer, P.G.5
Hughes, D.6
Reider, P.J.7
-
13
-
-
0345003850
-
-
(i) Nemes, P.; Balázs, B.; Tóth, G.; Scheiber, P. Synlett 1999, 222.
-
(1999)
Synlett
, pp. 222
-
-
Nemes, P.1
Balázs, B.2
Tóth, G.3
Scheiber, P.4
-
14
-
-
0001327019
-
-
(j) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698.
-
(1999)
Acta Crystallogr.
, vol.55
, pp. 1698
-
-
Hua, D.H.1
Chen, Y.2
Sin, H.-S.3
Robinson, P.D.4
Meyers, C.Y.5
Perchellet, E.M.6
Perchellet, J.-P.7
Chiang, P.K.8
Biellmann, J.-P.9
-
15
-
-
0032565066
-
-
Also see: (a) P. Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 2493
-
-
Benovsky, P.1
Stephenson, G.A.2
Stille, J.R.3
-
19
-
-
37049102818
-
-
(e) Chaaban, J.; Greenhill, J. V.; Rauli, M. J. Chem. Soc., Perkin Trans, 1 1981, 3120.
-
(1981)
J. Chem. Soc., Perkin Trans, 1
, pp. 3120
-
-
Chaaban, J.1
Greenhill, J.V.2
Rauli, M.3
-
21
-
-
4644248178
-
-
For intermolecular formal aza-[3 + 3] cycloadditions, see: (a) Sydorenko, N.; Hsung R. P.; Darwish, O. S.; Hahn, J. M.; Liu, J. J. Org. Chem. 2004, 69, 6732.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6732
-
-
Sydorenko, N.1
Hsung, R.P.2
Darwish, O.S.3
Hahn, J.M.4
Liu, J.5
-
22
-
-
0037019536
-
-
(b) Sklenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.-L.; Gerasyuto, A. I.; Brennessel, W. W. J. Am. Chem. Soc. 2002, 124, 10435.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 10435
-
-
Sklenicka, H.M.1
Hsung, R.P.2
McLaughlin, M.J.3
Wei, L.-L.4
Gerasyuto, A.I.5
Brennessel, W.W.6
-
23
-
-
0000193493
-
-
(c) Sklenicka, H. M.; Hsung, R. P.; Wei, L.-L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen, S. J.; Mulder, J. A. Org. Lett. 2000, 2, 1161.
-
(2000)
Org. Lett.
, vol.2
, pp. 1161
-
-
Sklenicka, H.M.1
Hsung, R.P.2
Wei, L.-L.3
McLaughlin, M.J.4
Gerasyuto, A.I.5
Degen, S.J.6
Mulder, J.A.7
-
24
-
-
0000546380
-
-
(d) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
-
(1999)
Org. Lett.
, vol.1
, pp. 509
-
-
Hsung, R.P.1
Wei, L.-L.2
Sklenicka, H.M.3
Douglas, C.J.4
McLaughlin, M.J.5
Mulder, J.A.6
Yao, L.J.7
-
25
-
-
0035901688
-
-
For intramolecular formal aza-[3 + 3] cycloaddition, see: Wei, L.-L.; Sklenicka, H. M.; Gerasyuto, A. I.; Hsung, R. P. Angew. Chem., Int. Ed. 2001, 40, 1516.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 1516
-
-
Wei, L.-L.1
Sklenicka, H.M.2
Gerasyuto, A.I.3
Hsung, R.P.4
-
26
-
-
0348041988
-
-
For our applications in natural product syntheses, see: (a) Luo, S.; Zificsak, C. Z.; Hsung, R. P. Org. Lett. 2003, 5, 4709.
-
(2003)
Org. Lett.
, vol.5
, pp. 4709
-
-
Luo, S.1
Zificsak, C.Z.2
Hsung, R.P.3
-
27
-
-
0037071942
-
-
(b) McLaughlin, M. J.; Hsung, R. P.; Cole, K. C.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
-
(2002)
Org. Lett.
, vol.4
, pp. 2017
-
-
McLaughlin, M.J.1
Hsung, R.P.2
Cole, K.C.3
Hahn, J.M.4
Wang, J.5
-
28
-
-
0000084271
-
-
The term "formal [3 + 3]" was used to describe [3 + 3] carbo-cycloadditions. See: (a) Seebach, D.; Missbach, M.; Calderari, G.; Eberle, M. J. Am. Chem. Soc. 1990, 112, 7625.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 7625
-
-
Seebach, D.1
Missbach, M.2
Calderari, G.3
Eberle, M.4
-
30
-
-
0001866893
-
-
For recent reviews on formal carbo-[3 + 3] cycloadditions using enamines, enol ethers, or β-ketoesters see: (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27.
-
(1999)
Chem. Rev.
, vol.99
, pp. 27
-
-
Filippini, M.-H.1
Rodriguez, J.2
-
31
-
-
0028810949
-
-
and see refs 21-33 cited within
-
(b) Filippini, M.-H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872, and see refs 21-33 cited within.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 6872
-
-
Filippini, M.-H.1
Faure, R.2
Rodriguez, J.3
-
32
-
-
19544386851
-
-
note
-
(c) For reviews on metal-mediated stepwise [3 + 3] cycloaddition reactions,
-
-
-
-
34
-
-
0002110351
-
-
(e) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
-
(1996)
Chem. Rev.
, vol.96
, pp. 49
-
-
Lautens, M.1
Klute, W.2
Tam, W.3
-
36
-
-
0011838270
-
-
Cordell, G. A., Ed.; Academic Press: New York
-
(b) Daly, J. W.: Garraffo, H. M.; Spande, T. F. The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, p 185.
-
(1993)
The Alkaloids
, vol.43
, pp. 185
-
-
Daly, J.W.1
Garraffo, H.M.2
Spande, T.F.3
-
38
-
-
0032913999
-
-
(d) Jones, T. H.; Gorman, J. S. T.; Snelling, R. R.; Delabie, J. H. C.; Slum, M. S.; Garraffo, H. M.; Jain, P.; Daly, J. W.; Spande, T. F. J. Chem. Ecol. 1999, 25, 1179.
-
(1999)
J. Chem. Ecol.
, vol.25
, pp. 1179
-
-
Jones, T.H.1
Gorman, J.S.T.2
Snelling, R.R.3
Delabie, J.H.C.4
Slum, M.S.5
Garraffo, H.M.6
Jain, P.7
Daly, J.W.8
Spande, T.F.9
-
41
-
-
0033709712
-
-
For a recent review on preparations of piperidines, see: Laschat, S.; Dickner, T. Synthesis 2000, 1781.
-
(2000)
Synthesis
, pp. 1781
-
-
Laschat, S.1
Dickner, T.2
-
42
-
-
0028920309
-
-
For leading references on electrocyclic ring-closures involving 1-azatrienes, see: (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem 1995, 60, 1763.
-
(1995)
J. Org. Chem
, vol.60
, pp. 1763
-
-
Maynard, D.F.1
Okamura, W.H.2
-
43
-
-
0024370013
-
-
(b) de Lera, A. R.; Reischl, W.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 4051.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 4051
-
-
De Lera, A.R.1
Reischl, W.2
Okamura, W.H.3
-
44
-
-
0000052960
-
-
For an earlier account, see: (c) Oppolzer, V. W. Angew. Chem. 1972, 22, 1108.
-
(1972)
Angew. Chem.
, vol.22
, pp. 1108
-
-
Oppolzer, V.W.1
-
45
-
-
0037151648
-
-
For recent elegant accounts on stereoselective ring-closure of 1-azatrienes, see: (a) Tanaka, K.; Katsumura, S. J. Am. Chem. Soc. 2002, 124, 9660.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9660
-
-
Tanaka, K.1
Katsumura, S.2
-
46
-
-
0035804974
-
-
(b) Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 3099
-
-
Tanaka, K.1
Mori, H.2
Yamamoto, M.3
Katsumura, S.4
-
47
-
-
4344562128
-
-
(c) Tanaka, K.; Kobayashi, T.; Mori, H.; Katsumura S. J. Org. Chem. 2004, 69, 5906.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 5906
-
-
Tanaka, K.1
Kobayashi, T.2
Mori, H.3
Katsumura, S.4
-
48
-
-
0000938909
-
-
Trost, B. M., Fleming, I., Eds.; Paquette, L. A., volume Ed.; Pergamon Press: New York
-
For a review on rotational preferences leading to diastereomeric induction during a 6π-electron electrocyclic ring closure see: Okamura, W. H.; de Lera, A. R. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Paquette, L. A., volume Ed.; Pergamon Press: New York, 1991; Vol. 5, pp 699-750.
-
(1991)
Comprehensive Organic Synthesis
, vol.5
, pp. 699-750
-
-
Okamura, W.H.1
De Lera, A.R.2
-
49
-
-
0037043180
-
-
For a recent review on proline-catalyzed asymmetric reactions see; List, B. Tetrahedron 2002, 58, 5573.
-
(2002)
Tetrahedron
, vol.58
, pp. 5573
-
-
List, B.1
-
50
-
-
4143094833
-
-
For a comprehensive set of reviews on asymmetric organocatalysis see: Acc. Chem. Res. 2004, 37, 487-631.
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 487-631
-
-
-
51
-
-
11844277087
-
-
(a) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 32
-
-
Ouellet, S.G.1
Tuttle, J.B.2
MacMillan, D.W.C.3
-
53
-
-
0037419866
-
-
(c) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1192
-
-
Brown, S.P.1
Goodwin, N.C.2
MacMillan, D.W.C.3
-
58
-
-
0034638388
-
-
(h) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9874
-
-
Jen, W.S.1
Wiener, J.J.M.2
MacMillan, D.W.C.3
-
59
-
-
0034600250
-
-
(i) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 4243
-
-
Ahrendt, K.A.1
Borths, C.J.2
MacMillan, D.W.C.3
-
60
-
-
4544361465
-
-
(a) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3958
-
-
Hechavarria Fonseca, M.T.1
List, B.2
-
61
-
-
1942437543
-
-
(b) List, B.; Hoang, L.; Martin, H. J. PNAS 2004, 101, 5839.
-
(2004)
PNAS
, vol.101
, pp. 5839
-
-
List, B.1
Hoang, L.2
Martin, H.J.3
-
64
-
-
0038729533
-
-
(e) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 2785
-
-
Pidathala, C.1
Hoang, L.2
Vignola, N.3
List, B.4
-
65
-
-
0037425534
-
-
(f) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 16
-
-
Hoang, L.1
Bahmanyar, S.2
Houk, K.N.3
List, B.4
-
67
-
-
8444223916
-
-
(a) Marigo, M.; Bachmann, S.; Halland, N.; Braunton, A.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 5507.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 5507
-
-
Marigo, M.1
Bachmann, S.2
Halland, N.3
Braunton, A.4
Jorgensen, K.A.5
-
69
-
-
2342614099
-
-
(c) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1272
-
-
Halland, N.1
Aburel, P.S.2
Jorgensen, K.A.3
-
70
-
-
0344835672
-
-
(d) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 1498
-
-
Juhl, K.1
Jorgensen, K.A.2
-
72
-
-
0037429423
-
-
(f) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 661
-
-
Halland, N.1
Aburel, P.S.2
Jorgensen, K.A.3
-
73
-
-
0037195702
-
-
(g) Halland, N.; Hazell, R. G.; Jorgensen, K. A. S. J. Org. Chem. 2002, 67, 8331.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 8331
-
-
Halland, N.1
Hazell, R.G.2
Jorgensen, K.A.S.3
-
74
-
-
0037024190
-
-
(h) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 6254
-
-
Kumaragurubaran, N.1
Juhl, K.2
Zhuang, W.3
Bogevig, A.4
Jorgensen, K.A.5
-
75
-
-
2442435852
-
-
(a) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 5962
-
-
Yamamoto, Y.1
Momiyama, N.2
Yamamoto, H.3
-
76
-
-
4243057730
-
-
(b) Hayashi, Y.; Yamaguchi, J.; Sumiya T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1112
-
-
Hayashi, Y.1
Yamaguchi, J.2
Sumiya, T.3
Shoji, M.4
-
79
-
-
19544377706
-
-
note
-
See the Supporting Information for details of all preparations, characterizations, and relevant Spartan'02 models.
-
-
-
-
80
-
-
0027400803
-
-
Yamamoto, Y.; Hoshino, J.; Fujimoto, Y.; Ohmoto, J.; Sawada, S. Synthesis 1993, 298.
-
(1993)
Synthesis
, pp. 298
-
-
Yamamoto, Y.1
Hoshino, J.2
Fujimoto, Y.3
Ohmoto, J.4
Sawada, S.5
-
81
-
-
19544367466
-
-
note
-
Attempts to dihydroxylate 11 only led to the isolation of the osmate ester A, but we were not successful in securing an X-ray structure of A.
-
-
-
-
84
-
-
0000766966
-
-
(a) Shiraiwa, T.; Shinjo, K.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 3251.
-
(1991)
Bull. Chem. Soc. Jpn.
, vol.64
, pp. 3251
-
-
Shiraiwa, T.1
Shinjo, K.2
Kurokawa, H.3
-
85
-
-
0014240342
-
-
(b) Portoghese, P. S.; Pazdernik, T. I.; Kuhn, W. L.; Kite, G.; Shafee, A. J. Med. Chem. 1968, 11, 12.
-
(1968)
Med. Chem.
, vol.11
, pp. 12
-
-
Portoghese, P.S.1
Pazdernik, T.I.2
Kuhn, W.L.3
Kite, G.4
Shafee, A.J.5
-
86
-
-
0038546766
-
-
Aggarwal, V. K.; Lopin, C.; Sandrinelli, F. J. Am. Chem. Soc. 2003, 125, 7596.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 7596
-
-
Aggarwal, V.K.1
Lopin, C.2
Sandrinelli, F.3
-
87
-
-
19544371399
-
-
note
-
Calculations were carried out in Spartan'02 software on a Dell Precision 650 Dual Xeon (2.00 GHz) workstation.
-
-
-
-
88
-
-
19544392553
-
-
Wavefunction, Inc.: 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612
-
Spartan'02, PC version; Wavefunction, Inc.: 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612; 2002.
-
(2002)
Spartan'02, PC Version
-
-
-
89
-
-
0035940126
-
-
Klumpp, D. A.; Aguirre, S. L.; Sanchez, G. V.; de Leon, S. J. Org. Lett. 2001, 31, 2781.
-
(2001)
Org. Lett.
, vol.31
, pp. 2781
-
-
Klumpp, D.A.1
Aguirre, S.L.2
Sanchez, G.V.3
De Leon, S.J.4
-
90
-
-
0037070070
-
-
Aggarwal, V. K.; Sandrinelli, F.; Charmant, J. P. H. Tetrahedron: Asymmetry 2002, 13, 87.
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 87
-
-
Aggarwal, V.K.1
Sandrinelli, F.2
Charmant, J.P.H.3
-
91
-
-
33748670720
-
-
Willems, J. G. H.; Hersmis, M. C.; de Gelder, R.; Smits, J. M. M.; Hammink, J. B.; Dommerholt, F. J.; Thijs, L.; Zwanenburg, B. J. Chem. Soc., Perkin Trans, 1 1997, 963.
-
(1997)
J. Chem. Soc., Perkin Trans, 1
, pp. 963
-
-
Willems, J.G.H.1
Hersmis, M.C.2
De Gelder, R.3
Smits, J.M.M.4
Hammink, J.B.5
Dommerholt, F.J.6
Thijs, L.7
Zwanenburg, B.8
|