-
1
-
-
0001253959
-
-
(a) Wendt, K. U.; Schulz, G. E.; Corey, E. J.; Liu, D. R. Angew. Chem., Int. Ed. 2000, 39, 2812.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2812
-
-
Wendt, K.U.1
Schulz, G.E.2
Corey, E.J.3
Liu, D.R.4
-
2
-
-
12044254693
-
-
(b) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
-
(1993)
Chem. Rev.
, vol.93
, pp. 2189
-
-
Abe, I.1
Rohmer, M.2
Prestwich, G.D.3
-
3
-
-
0003939537
-
-
Breslow, R., Karplus, M., Eds.; W. A. Benjamin, Inc.: New York
-
(c) Richards, J. H.; Hendrickson, J. B. In The Biosynthesis of Steroids, Terpenes, and Acetogenins; Breslow, R., Karplus, M., Eds.; W. A. Benjamin, Inc.: New York, 1964.
-
(1964)
The Biosynthesis of Steroids, Terpenes, and Acetogenins
-
-
Richards, J.H.1
Hendrickson, J.B.2
-
4
-
-
0001418150
-
-
Morrison, J. D., Ed.; Academic Press: Orlando
-
(a) Bartlet, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1984; Vol. 3, p 342.
-
(1984)
Asymmetric Synthesis
, vol.3
, pp. 342
-
-
Bartlet, P.A.1
-
5
-
-
0001140189
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, England
-
(b) Sutherland, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, England, 1991; Vol. 3, p 341.
-
(1991)
Comprehensive Organic Synthesis
, vol.3
, pp. 341
-
-
Sutherland, J.K.1
-
6
-
-
0033601170
-
-
and references therein
-
See ref 2 and also: (a) Johnson, W. S.; Bartlett, W. R.; Czeskis, B. A.; Gautier, A.; Lee, C. H.; Lemoine, R.; Leopold, E. J.; Luedtke, G. R.; Bancroft, K. J. J. Org. Chem. 1999, 64, 9587 and references therein, (b) Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2002, 124, 3647. (c) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Org. Chem. 1986, 51, 806. (d) Corey, E. J.; Wood, H. B. J. Am. Chem. Soc. 1996, 118, 11982 and references therein.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 9587
-
-
Johnson, W.S.1
Bartlett, W.R.2
Czeskis, B.A.3
Gautier, A.4
Lee, C.H.5
Lemoine, R.6
Leopold, E.J.7
Luedtke, G.R.8
Bancroft, K.J.9
-
7
-
-
0037051649
-
-
See ref 2 and also: (a) Johnson, W. S.; Bartlett, W. R.; Czeskis, B. A.; Gautier, A.; Lee, C. H.; Lemoine, R.; Leopold, E. J.; Luedtke, G. R.; Bancroft, K. J. J. Org. Chem. 1999, 64, 9587 and references therein, (b) Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2002, 124, 3647. (c) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Org. Chem. 1986, 51, 806. (d) Corey, E. J.; Wood, H. B. J. Am. Chem. Soc. 1996, 118, 11982 and references therein.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3647
-
-
Ishihara, K.1
Ishibashi, H.2
Yamamoto, H.3
-
8
-
-
33845376064
-
-
See ref 2 and also: (a) Johnson, W. S.; Bartlett, W. R.; Czeskis, B. A.; Gautier, A.; Lee, C. H.; Lemoine, R.; Leopold, E. J.; Luedtke, G. R.; Bancroft, K. J. J. Org. Chem. 1999, 64, 9587 and references therein, (b) Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2002, 124, 3647. (c) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Org. Chem. 1986, 51, 806. (d) Corey, E. J.; Wood, H. B. J. Am. Chem. Soc. 1996, 118, 11982 and references therein.
-
(1986)
J. Org. Chem.
, vol.51
, pp. 806
-
-
Nishizawa, M.1
Takenaka, H.2
Hayashi, Y.3
-
9
-
-
0029902231
-
-
and references therein
-
See ref 2 and also: (a) Johnson, W. S.; Bartlett, W. R.; Czeskis, B. A.; Gautier, A.; Lee, C. H.; Lemoine, R.; Leopold, E. J.; Luedtke, G. R.; Bancroft, K. J. J. Org. Chem. 1999, 64, 9587 and references therein, (b) Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2002, 124, 3647. (c) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Org. Chem. 1986, 51, 806. (d) Corey, E. J.; Wood, H. B. J. Am. Chem. Soc. 1996, 118, 11982 and references therein.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 11982
-
-
Corey, E.J.1
Wood, H.B.2
-
10
-
-
0025269877
-
-
See, for example, Bright, S. T.; Coxon, J. M.; Steel, P. J. J. Org. Chem. 1990, 55, 1338.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 1338
-
-
Bright, S.T.1
Coxon, J.M.2
Steel, P.J.3
-
12
-
-
0001152417
-
-
Trost, B. M., Ed.; Pergamon Press
-
(b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: 1991; Vol. 4, p 571.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 571
-
-
Hegedus, L.S.1
-
13
-
-
0037036759
-
-
Hahn, C.; Cucciolito, M. E.; Vitagliano, A. J. Am. Chem. Soc. 2002, 124, 9038.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9038
-
-
Hahn, C.1
Cucciolito, M.E.2
Vitagliano, A.3
-
14
-
-
0038306262
-
-
(a) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J. Tetrahedron 2003, 59, 5623.
-
(2003)
Tetrahedron
, vol.59
, pp. 5623
-
-
Taylor, R.E.1
Engelhardt, F.C.2
Schmitt, M.J.3
-
15
-
-
0038561146
-
-
(b) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625.
-
(2003)
Chem. Rev.
, vol.103
, pp. 1625
-
-
Wessjohann, L.A.1
Brandt, W.2
Thiemann, T.3
-
16
-
-
0037692311
-
-
Diene cycloisomerization processes do not typically give cyclopropanes; see: (a) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215. (b) Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 215
-
-
Lloyd-Jones, G.C.1
-
17
-
-
0036798179
-
-
Diene cycloisomerization processes do not typically give cyclopropanes; see: (a) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215. (b) Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905.
-
(2002)
Acc. Chem. Res.
, vol.35
, pp. 905
-
-
Widenhoefer, R.A.1
-
18
-
-
1842483218
-
-
Ene-ynes, on the other hand, do typically give cyclopropanes: (c) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
-
(2004)
Chem. Rev.
, vol.104
, pp. 1317
-
-
Diver, S.T.1
Giessert, A.J.2
-
19
-
-
3242741475
-
-
For a recent Au(I) catalyst, see: (d) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 2402
-
-
Nieto-Oberhuber, C.1
Muñoz, M.P.2
Buñuel, E.3
Nevado, C.4
Cárdenas, D.J.5
Echavarren, A.M.6
-
20
-
-
4444341440
-
-
note
-
This nomenclature first refers to the bond being activated and then the nucleophilic bond.
-
-
-
-
21
-
-
4444225192
-
-
Koh, J. H., Gagné, M. R. Angew. Chem., Int. Ed. 2004, 43, 3459.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3459
-
-
Koh, J.H.1
Gagné, M.R.2
-
22
-
-
0037420330
-
-
Cation-olefin cyclizations with oxonium initiators also proceed selectively via this conformer; see ref 2a and: (a) Seiders, J. R., II; Wang, L.; Floreancig, P. E. J. Am. Chem. Soc. 2003, 125, 2406. (b) Johnson, W. S.; van der Gen, A.; Swoboda, J. J. J. Am. Chem. Soc. 1967, 89, 170.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 2406
-
-
Seiders II, J.R.1
Wang, L.2
Floreancig, P.E.3
-
23
-
-
4444368623
-
-
Cation-olefin cyclizations with oxonium initiators also proceed selectively via this conformer; see ref 2a and: (a) Seiders, J. R., II; Wang, L.; Floreancig, P. E. J. Am. Chem. Soc. 2003, 125, 2406. (b) Johnson, W. S.; van der Gen, A.; Swoboda, J. J. J. Am. Chem. Soc. 1967, 89, 170.
-
(1967)
J. Am. Chem. Soc.
, vol.89
, pp. 170
-
-
Johnson, W.S.1
Van Der Gen, A.2
Swoboda, J.J.3
-
26
-
-
0013649939
-
-
(c) McWilliam, D. C.; Balasubramanian, T. R.; Kuivila, H. G. J. Am. Chem. Soc. 1978, 100, 6407.
-
(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 6407
-
-
McWilliam, D.C.1
Balasubramanian, T.R.2
Kuivila, H.G.3
-
27
-
-
0000506691
-
-
(d) Lambert, J. B.; Salvador, L. A.; So, J. H. Organometallics 1993, 12, 697.
-
(1993)
Organometallics
, vol.12
, pp. 697
-
-
Lambert, J.B.1
Salvador, L.A.2
So, J.H.3
-
30
-
-
0000723905
-
-
(c) Brookhart, M.; Liu, Y.; Goldman, E. W.; Timmers, D. A.; Williams, G. D. J. Am. Chem. Soc. 1991, 113, 927.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 927
-
-
Brookhart, M.1
Liu, Y.2
Goldman, E.W.3
Timmers, D.A.4
Williams, G.D.5
-
33
-
-
4444369214
-
-
note
-
Friedel-Craft-type cyclization on the activated ortho positions is intuitively reasonable, though we have no proof at this time.
-
-
-
-
34
-
-
0037144642
-
-
For recent examples, see: (a) Nagumo, S.; Ono, M.; Kakimoto, Y.; Furukawa, T.; Hisano. T.; Mizukami, M.; Kawahara, N.; Akita, H. J. Org. Chem. 2002, 67, 6618. (b) Nagumo, S.; Ishii, Y.; Kakimoto, Y.; Kawahara, N. Tetrahedron Lett. 2002, 43, 5333.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 6618
-
-
Nagumo, S.1
Ono, M.2
Kakimoto, Y.3
Furukawa, T.4
Hisano, T.5
Mizukami, M.6
Kawahara, N.7
Akita, H.8
-
35
-
-
0037158212
-
-
For recent examples, see: (a) Nagumo, S.; Ono, M.; Kakimoto, Y.; Furukawa, T.; Hisano. T.; Mizukami, M.; Kawahara, N.; Akita, H. J. Org. Chem. 2002, 67, 6618. (b) Nagumo, S.; Ishii, Y.; Kakimoto, Y.; Kawahara, N. Tetrahedron Lett. 2002, 43, 5333.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 5333
-
-
Nagumo, S.1
Ishii, Y.2
Kakimoto, Y.3
Kawahara, N.4
-
36
-
-
0032997636
-
-
(a) Schmidt, C. O.; Bouwmeester, H. J.; Franke, S.; König, W. A. Chirality 1999, 11, 353.
-
(1999)
Chirality
, vol.11
, pp. 353
-
-
Schmidt, C.O.1
Bouwmeester, H.J.2
Franke, S.3
König, W.A.4
-
38
-
-
0002824973
-
-
Alternative 1,4- or 1,5-transfers from the ring are also possible, (a) Saunders: M.; Jimenez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (b) Watt, C. I. F. In Advances in Physical Organic Chemistry, Bethell, D., Ed.; Academic Press: New York, 1988; Vol. 24, p 57.
-
(1991)
Chem. Rev.
, vol.91
, pp. 375
-
-
Saunders, M.1
Jimenez-Vazquez, H.A.2
-
39
-
-
0002680167
-
-
Bethell, D., Ed.; Academic Press: New York
-
Alternative 1,4- or 1,5-transfers from the ring are also possible, (a) Saunders: M.; Jimenez-Vazquez, H. A. Chem. Rev. 1991, 91, 375. (b) Watt, C. I. F. In Advances in Physical Organic Chemistry, Bethell, D., Ed.; Academic Press: New York, 1988; Vol. 24, p 57.
-
(1988)
Advances in Physical Organic Chemistry
, vol.24
, pp. 57
-
-
Watt, C.I.F.1
-
40
-
-
4444336167
-
-
note
-
Control experiments showed that 1b catalyzes the isomerization of 4,4-dimethylcyclohexene to 3,3-dimethylcyclohexene.
-
-
-
-
41
-
-
4444231825
-
-
note
-
Pt catalysts 1a and 1b are completely selective for 3 and 5, respectively. No traces of cyclohexenes were detected (GC) in the crude cyclopropane reaction mixtures, and vice versa.
-
-
-
-
42
-
-
33748726159
-
-
Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 798
-
-
Evans, D.A.1
Murry, J.A.2
Von Matt, P.3
Norcross, R.D.4
Miller, S.J.5
|