SCOPUS 정보 검색 플랫폼

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4149-4151

On the Diastereoselectivity of Ru-Catalyzed [5 + 2] Cycloadditions

(5) Trost, Barry M a Shen, Hong C a Schulz, Tobias a Koradin, Christopher a Schirok, Hartmut a

a STANFORD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZULENE; CYCLOPROPANE DERIVATIVE; RUTHENIUM;

ALDER; ARTICLE; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; ISOMERISM; STEREOCHEMISTRY;

ALKENES; ALKYNES; AZULENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOHEPTANES; CYCLOPROPANES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 0344944923 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0355884 Document Type: Article

Times cited : (54)

References (35)

1
- 0002110351
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (1996) Chem. Rev. , vol.96 , pp. 49
- Lautens, M.¹ Klute, W.² Tam, W.³

2
- 0031138748
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (1997) Coord. Chem. Rev. , vol.161 , pp. 129
- Hegedus, L.S.¹

3
- 0002554473
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (1997) Contemp. Org. Synth. , vol.4 , pp. 87
- Dell, C.P.¹

4
- 0031146501
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (1997) Chem. Rev. , vol.97 , pp. 523
- Fruhauf, H.-W.¹

5
- 0001866893
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (1999) Chem. Rev. , vol.99 , pp. 27
- Filippini, M.-H.¹ Rodriguez, J.²

6
- 0034246704
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (2000) Chem. Rev. , vol.100 , pp. 2963
- Yet, L.¹

7
- 0000463815
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (1996) Chem. Rev. , vol.96 , pp. 635
- Ojima, I.¹ Tzamariousdaki, M.² Li, Z.³ Donovan, R.J.⁴

8
- 0344237307
- Ph.D. Thesis, Stanford University, Stanford, CA
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (2001)
- Love, J.A.¹

9
- 0034696037
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 477
- Hartley, R.C.¹ Caldwell, S.T.²

10
- 0036291655
- For reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. (d) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523. (e) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27. (f) Yet, L. Chem. Rev. 2000, 100, 2963. (g) Ojima, I.; Tzamariousdaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (h) Love, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2001. (i) Hartley, R. C. ; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (j) Wender, P. A. Pure Appl. Chem. 2002, 74, 25.
- (2002) Pure Appl. Chem. , vol.74 , pp. 25
- Wender, P.A.¹

11
- 33750309194
- (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
- (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 259
- Trost, B.M.¹

12
- 0742298948
- (b) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
- (1998) Synlett , pp. 1
- Trost, B.M.¹ Krische, M.J.²

13
- 0028956752
- (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 112, 4720.
- (1995) J. Am. Chem. Soc. , vol.112 , pp. 4720
- Wender, P.A.¹ Takahashi, H.² Witulski, B.³

14
- 0032481586
- (b) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1940
- Wender, P.A.¹ Husfeld, C.O.² Langkopf, E.³ Love, J.A.⁴

15
- 0032543523
- (c) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203.
- (1998) Tetrahedron , vol.54 , pp. 7203
- Wender, P.A.¹ Husfeld, C.O.² Langkopf, E.³ Love, J.A.⁴ Pleuss, N.⁵

16
- 0000625477
- (d) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164.
- (1998) J. Org. Chem. , vol.63 , pp. 4164
- Wender, P.A.¹ Sperandio, D.²

17
- 0033538287
- (e) Wender, P. A.; Glorius, F.; Husfield, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5348
- Wender, P.A.¹ Glorius, F.² Husfield, C.O.³ Langkopf, E.⁴ Love, J.A.⁵

18
- 0000678991
- (f) Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137.
- (1999) Org. Lett. , vol.1 , pp. 137
- Wender, P.A.¹ Fuji, M.² Husfeld, C.O.³ Love, J.A.⁴

19
- 0032576188
- (g) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 10976
- Wender, P.A.¹ Rieck, H.² Fuji, M.³

20
- 0001301163
- (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609.
- (2000) Org. Lett. , vol.2 , pp. 1609
- Wender, P.A.¹ Dyckman, A.J.² Husfeld, C.O.³ Scanio, M.J.C.⁴

21
- 0035835039
- (i) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 170.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 170
- Wender, P.A.¹ Barzilay, C.M.² Dyckman, A.J.³

22
- 0037176267
- (j) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 15154
- Wender, P.A.¹ Pedersen, T.M.² Scanio, M.J.C.³

23
- 0001758137
- (k) Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 13, 2089.
- (1999) Org. Lett. , vol.13 , pp. 2089
- Wender, P.A.¹ Dyckman, A.J.²

24
- 0037011303
- (l) 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

25
- 0035886047
- (m) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895.
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3895
- Wender, P.A.¹ Gamber, G.G.² Scanio, M.J.C.³

26
- 0030694422
- (a) Trost, B. M.; Drause, L.; Portnoy, M. J. Am. Chem. Soc. 1997, 119, 11319.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 11319
- Trost, B.M.¹ Drause, L.² Portnoy, M.³

27
- 0032538014
- (b) Trost, B. M.; Probst, G. D.; Schoop, A. J. Am. Chem. Soc. 1998, 120, 9228.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 9228
- Trost, B.M.¹ Probst, G.D.² Schoop, A.³

28
- 0031047428
- (c) Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 836
- Trost, B.M.¹ Portnoy, M.² Kurihara, H.³

29
- 0034654486
- (a) Trost, B. M.; Toste, F. D.; Shen. H. J. Am. Chem. Soc. 2000, 122, 2379.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2379
- Trost, B.M.¹ Toste, F.D.² Shen, H.³

30
- 0035907913
- (b) Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313.
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2313
- Trost, B.M.¹ Shen, H.C.²

31
- 0034632403
- (c) Trost, B. M.; Shen, H. C. Org. Lett. 2000, 2, 2523.
- (2000) Org. Lett. , vol.2 , pp. 2523
- Trost, B.M.¹ Shen, H.C.²

32
- 0037178098
- Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2002, 124, 7376.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 7376
- Trost, B.M.¹ Pinkerton, A.B.²

33
- 0030768660
- (a) Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 8031.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 8031
- Haller, J.¹ Strassner, T.² Houk, K.N.³

34
- 33845471903
- (b) Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Jäger, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 3880
- Houk, K.N.¹ Moses, S.R.² Wu, Y.-D.³ Rondan, N.G.⁴ Jäger, V.⁵ Schohe, R.⁶ Fronczek, F.R.⁷

35
- 0000600645
- (c) Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 24, 3951.
- (1983) Tetrahedron Lett. , vol.24 , pp. 3951
- Stork, G.¹ Kahn, M.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.