SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 11, 2007, Pages 1663-1666

Ring-rearrangement metathesis of substituted 2-aminonorbornenes

(2) Nadany, Adam E a Mckendrick, John E a

a UNIVERSITY OF READING (United Kingdom)

Author keywords

Diels Alder reaction; Metathesis; Piperidine alkaloids

Indexed keywords

2 AMINONORBORNENE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMIDE; AMINE; N BENZYL 2 AMINOBORNENE; NORBORNENE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING;

EID: 34447544571 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-982573 Document Type: Article

Times cited : (5)

References (54)

1
- 85004258725
- (a) Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6889.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 6889
- Bazan, G.C.¹ Oskam, J.H.² Cho, H.N.³ Park, L.Y.⁴ Schrock, R.R.⁵

2
- 0001684171
- (b) Bazan, G. C.; Khosravi, E.; Schrock, R. R.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Thomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 8378
- Bazan, G.C.¹ Khosravi, E.² Schrock, R.R.³ Feast, W.J.⁴ Gibson, V.C.⁵ O'Regan, M.B.⁶ Thomas, J.K.⁷ Davis, W.M.⁸

3
- 0033516491
- (c) Schrock, R. R. Tetrahedron 1999, 55, 8141.
- (1999) Tetrahedron , vol.55 , pp. 8141
- Schrock, R.R.¹

4
- 0001422883
- (d) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158.
- (1990) Acc. Chem. Res , vol.23 , pp. 158
- Schrock, R.R.¹

5
- 84989561615
- (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 9858
- Nguyen, S.T.¹ Grubbs, R.H.² Ziller, J.W.³

6
- 0001855961
- (b) Scwabb, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 100
- Scwabb, P.¹ Grubbs, R.H.² Ziller, J.W.³

7
- 0034734340
- (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 8168
- Garber, S.B.¹ Kingsbury, J.S.² Gray, B.L.³ Hoveyda, A.H.⁴

8
- 0037463719
- (b) Dunne, A. M.; Mix, S.; Blechert, S. Tetrahedron 2003, 59, 2733.
- (2003) Tetrahedron , vol.59 , pp. 2733
- Dunne, A.M.¹ Mix, S.² Blechert, S.³

9
- 0142023994
- For reviews on the history, synthesis, and activity of the molybdenum-based metathesis catalysts, see: a
- For reviews on the history, synthesis, and activity of the molybdenum-based metathesis catalysts, see: (a) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4592
- Schrock, R.R.¹ Hoveyda, A.H.²

10
- 0344006321
- For recent reviews on ruthenium-based RCM, see: b
- For recent reviews on ruthenium-based RCM, see: (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3012
- Fürstner, A.¹

11
- 0034746687
- (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
- (2001) Acc. Chem. Res , vol.34 , pp. 18
- Trnka, T.M.¹ Grubbs, R.H.²

12
- 0038215596
- Blechert, S.; Connon, S. J. Angew. Chem. Int. Ed. 2003, 42, 1900.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1900
- Blechert, S.¹ Connon, S.J.²

13
- 0033516690
- (a) Stragies, R.; Blechert, S. Tetrahedron 1999, 8179.
- (1999) Tetrahedron , pp. 8179
- Stragies, R.¹ Blechert, S.²

14
- 17644420655
- (b) Pfeiffer, M. W. B.; Phillips, A. J. J. Am. Chem. Soc. 2005, 127, 5334.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 5334
- Pfeiffer, M.W.B.¹ Phillips, A.J.²

15
- 7044239530
- (c) Winkler, J. D.; Asselin, S. M.; Shepard, S.; Yuan, J. Org. Lett. 2004, 6, 3821.
- (2004) Org. Lett , vol.6 , pp. 3821
- Winkler, J.D.¹ Asselin, S.M.² Shepard, S.³ Yuan, J.⁴

16
- 2342633115
- (d) Wrobleski, A.; Sahasrabudhe, K.; Aube, J. J. Am. Chem. Soc. 2004, 126, 5475.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 5475
- Wrobleski, A.¹ Sahasrabudhe, K.² Aube, J.³

17
- 23944513776
- (e) Chandler, C. L.; Phillips, A. J. Org. Lett. 2005, 7, 3493.
- (2005) Org. Lett , vol.7 , pp. 3493
- Chandler, C.L.¹ Phillips, A.J.²

18
- 10044263386
- (f) Yasui, H.; Yamamoto, S.; Saaki, D.; Kawasaki, S.; Watanabe, G.; Tadano, K.-I. J. Org. Chem. 2004, 69, 8789.
- (2004) J. Org. Chem , vol.69 , pp. 8789
- Yasui, H.¹ Yamamoto, S.² Saaki, D.³ Kawasaki, S.⁴ Watanabe, G.⁵ Tadano, K.-I.⁶

19
- 2942629125
- (g) Boyer, F.-D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817.
- (2004) Org. Lett , vol.6 , pp. 1817
- Boyer, F.-D.¹ Hanna, I.² Ricard, L.³

20
- 9444286984
- (h) Quinn, K. J.; Isaacs, A. K.; Arvary, R. A. Org. Lett. 2004, 6, 4143.
- (2004) Org. Lett , vol.6 , pp. 4143
- Quinn, K.J.¹ Isaacs, A.K.² Arvary, R.A.³

21
- 4143072880
- (i) Lesma, G.; Crippa, S.; Danieli, B.; Passarella, D.; Sacchetti, A.; Silvani, A.; Virdis, A. Tetrahedron 2004, 60, 6437.
- (2004) Tetrahedron , vol.60 , pp. 6437
- Lesma, G.¹ Crippa, S.² Danieli, B.³ Passarella, D.⁴ Sacchetti, A.⁵ Silvani, A.⁶ Virdis, A.⁷

22
- 22144431616
- (j) Csaky, A. G.; Medel, R.; Murcia, M. C.; Plumet, J. Helv. Chim. Acta 2005, 88, 1387.
- (2005) Helv. Chim. Acta , vol.88 , pp. 1387
- Csaky, A.G.¹ Medel, R.² Murcia, M.C.³ Plumet, J.⁴

23
- 34447505105
- Handbook of Metathesis, 2; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003, Chap. 2-4, 151-175.
- Handbook of Metathesis, Vol. 2; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003, Chap. 2-4, 151-175.

24
- 0034627348
- Arjona, O.; Csaky, A. G.; Murica, M. C.; Plumet, J. Tetrahedron Lett. 2000, 41, 9777.
- (2000) Tetrahedron Lett , vol.41 , pp. 9777
- Arjona, O.¹ Csaky, A.G.² Murica, M.C.³ Plumet, J.⁴

25
- 0035974356
- Ruckert, A.; Reisele, D.; Blechert, S. Tetrahedron Lett. 2001, 42, 5245.
- (2001) Tetrahedron Lett , vol.42 , pp. 5245
- Ruckert, A.¹ Reisele, D.² Blechert, S.³

26
- 0037067875
- Hagiwara, H.; Katsumi, T.; Endou, S.; Hoshi, T.; Suzuki, T. Tetrahedron 2002, 58, 6651.
- (2002) Tetrahedron , vol.58 , pp. 6651
- Hagiwara, H.¹ Katsumi, T.² Endou, S.³ Hoshi, T.⁴ Suzuki, T.⁵

27
- 0034051322
- (a) Voightmann, U.; Blechert, S. Synthesis 2000, 893.
- (2000) Synthesis , pp. 893
- Voightmann, U.¹ Blechert, S.²

28
- 0035912321
- (b) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161.
- (2001) Org. Lett , vol.3 , pp. 1161
- Kitamura, T.¹ Mori, M.²

29
- 0037048460
- (c) Ovaa, H.; Stapper, C.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H.; Blechert, S. Tetrahedron 2002, 58, 7503.
- (2002) Tetrahedron , vol.58 , pp. 7503
- Ovaa, H.¹ Stapper, C.² van der Marel, G.A.³ Overkleeft, H.S.⁴ van Boom, J.H.⁵ Blechert, S.⁶

30
- 0037154809
- (d) Arjona, O.; Csaky, A. G.; Medel, R.; Plumet, J. J. Org. Chem. 2002, 67, 1380.
- (2002) Org. Chem , vol.67 , pp. 1380
- Arjona, O.¹ Csaky, A.G.² Medel, R.³ Plumet, J.J.⁴

31
- 0013354851
- (e) Arjona, O.; Csaky, A. G.; Murcia, C.; Plumet, J. ARKIVOC 2002, (v), 171.
- (2002) ARKIVOC , pp. 171
- Arjona, O.¹ Csaky, A.G.² Murcia, C.³ Plumet, J.⁴

32
- 0347624536
- (f) Arjona, O.; Csaky, A. G.; Leon, V.; Medel, R.; Plumet, J. Tetrahedron Lett. 2004, 45, 565.
- (2004) Tetrahedron Lett , vol.45 , pp. 565
- Arjona, O.¹ Csaky, A.G.² Leon, V.³ Medel, R.⁴ Plumet, J.⁵

33
- 17444431613
- (g) Holub, N.; Neidhofer, J.; Blechert, S. Org. Lett. 2005, 7, 1227.
- (2005) Org. Lett , vol.7 , pp. 1227
- Holub, N.¹ Neidhofer, J.² Blechert, S.³

34
- 33846925880
- (h) Groaz, E.; Banti, D.; North, M. Tetrahedron Lett. 2007, 48, 1927.
- (2007) Tetrahedron Lett , vol.48 , pp. 1927
- Groaz, E.¹ Banti, D.² North, M.³

35
- 28644448266
- (a) Maechling, S.; Norman, S. E.; Mckendrick, J. E.; Basra, S.; Knoppner, K.; Blechert, S. Tetrahedron Lett. 2006, 47, 189.
- (2006) Tetrahedron Lett , vol.47 , pp. 189
- Maechling, S.¹ Norman, S.E.² Mckendrick, J.E.³ Basra, S.⁴ Knoppner, K.⁵ Blechert, S.⁶

36
- 33748276631
- (b) Nadany, A. E.; Mckendrick, J. E. Synlett 2006, 2139.
- (2006) Synlett , pp. 2139
- Nadany, A.E.¹ Mckendrick, J.E.²

37
- 34247893691
- (c) Nadany, A. E.; Mckendrick, J. E. Tetrahedron Lett. 2007, 48, 4071.
- (2007) Tetrahedron Lett , vol.48 , pp. 4071
- Nadany, A.E.¹ Mckendrick, J.E.²

38
- 34447530959
- (a) Krieger, H. Suom. Kemistil., B 1963, 36, 68.
- (1963) Suom. Kemistil., B , vol.36 , pp. 68
- Krieger, H.¹

39
- 33947326853
- (b) Freeman, P. K.; Balls, D. M.; Brown, D. J. J. Org. Chem. 1968, 33, 2211.
- (1968) J. Org. Chem , vol.33 , pp. 2211
- Freeman, P.K.¹ Balls, D.M.² Brown, D.J.³

40
- 0021915493
- (a) Longobardi, M.; Schenone, P.; Bargagna, A.; Berrino, L.; Matera, C.; Marmo, E. Farmco Ed. Sci. 1985, 40, 152.
- (1985) Farmco Ed. Sci , vol.40 , pp. 152
- Longobardi, M.¹ Schenone, P.² Bargagna, A.³ Berrino, L.⁴ Matera, C.⁵ Marmo, E.⁶

41
- 0000844109
- (b) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
- (1996) J. Org. Chem , vol.61 , pp. 3849
- Abdel-Magid, A.F.¹ Carson, K.G.² Harris, B.D.³ Maryanoff, C.A.⁴ Shah, R.D.⁵

42
- 0035958505
- Analogous reduction of norborn-5-en-2-one: (c) Mayo, P.; Orlova, G.; Goddard, J. D.; Tam, W. J. Org. Chem. 2001, 66, 5182.
- Analogous reduction of norborn-5-en-2-one: (c) Mayo, P.; Orlova, G.; Goddard, J. D.; Tam, W. J. Org. Chem. 2001, 66, 5182.

43
- 84987584120
- (d) Oppolzer, W.; Chapuis, C.; Dupuis, D.; Guo, M. Helv. Chim. Acta 1985, 68, 2100.
- (1985) Helv. Chim. Acta , vol.68 , pp. 2100
- Oppolzer, W.¹ Chapuis, C.² Dupuis, D.³ Guo, M.⁴

44
- 34447540269
- Spectroscopic Data for 5a 1H NMR (400 MHz, CDCl 3, 70°C, δ, 1.35-1.38 (m, 1 H, CH2CHN, 1.35-1.38 (m, 1 H, CH2CHCHN, 2.12-2.33 (m, 1 H, CH2CHN, 2.12-2.33 (m, 1 H, CH2CHCHN, 2.12-2.33 (m, 1 H, CHCH 2CHN, 2.90-2.94 (m, 1 H, CHCHN, 3.69 (dt, 1 H, CHN, J, 10.5, 6.5 Hz, 4.06 (d, 1 H, CH2Ph, J, 15.0 Hz, 4.90-5.03 (m, 2 H, CH=CH2, 5.29 (d, 1 H, CH2Ph, J, 15.0 Hz, 5.71 (ddd, 1 H, CH=CH2, J, 17.0, 13.0,7.0 Hz, 5.87 (dd, 1 H, HC=CH, J, 10.0, 2.5 Hz, 6.24 (dd, 1 H, HC=CH, J, 10.0, 3.0 Hz, 7.25-7.33 (m, 5 H, 5 x ArH, 13C NMR (100 MHz, CDCl 3, 70°C, δ, 36.6 (CHCHN, 38.6 (CH2CHCHN, 39.0 (CH2CHN, 40.1 (CHCH2CHN, 48.5 (CH2Ph, 58.7 (CHN, 114.5 (CH=CH2, 122.0 (HC=CH, 127.8 (1 x ArH, 128.4 (2 x ArH, 129.0 2 x
- +]; found: 254.1546.

45
- 0038163433
- Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 9130
- Fürstner, A.¹ Langemann, K.²

46
- 0001768322
- Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 12388
- Kinoshita, A.¹ Sakakibara, N.² Mori, M.³

47
- 34447513193
- General Procedure for Olefin Metathesis, Synthesis of 8c A flask was charged with toluenesulfonyl amine 7c (91 mg, 0.3 mmol) and CH 2Cl2 (90 mL, Ethene gas was bubbled through the solution for 20 s. Then, Grubbs I catalyst (25 mg, 0.03 mmol) was added to the reaction. A balloon filled with ethene gas was placed over the flask and the reaction was allowed to stir at r.t. overnight. The reaction mixture was then concentrated and subjected to column chromatography eluting PE-Et2O (19:1 to 4:1) to furnish 8c as a colourless oil (89 mg, 99% yield. 1H NMR (400 MHz, CDCl3, δ, 1.11 (ddd, 1 H, CH2CHN, J, 13.5, 8.0, 4.0 Hz, 1.33 (dd, 1 H, H2CHCHC=CH, J, 14.5, 7.5 Hz, 1.66 (dt, 1 H, H2CHCHC=CH, J, 12.0, 6.5 Hz, 2.13 (td, 1 H, CH2CHN, J, 16.0, 13.5 Hz, 2.41 (s, 3 H, CH3, 2.41-2.43 (m, 1 H, HCHC=CH, 2.60-2.65 brm, 1 H, HC
- +]; found: 303.1293.

48
- 0040943788
- Parham, W. E.; Hunter, W. T.; Hanson, R. J. Am. Chem. Soc. 1951, 73, 5068.
- (1951) J. Am. Chem. Soc , vol.73 , pp. 5068
- Parham, W.E.¹ Hunter, W.T.² Hanson, R.³

49
- 10044287337
- (a) Fangzheng, L.; Warshakoon, N. C.; Miller, M. J. J. Org. Chem. 2004, 69, 8836.
- (2004) J. Org. Chem , vol.69 , pp. 8836
- Fangzheng, L.¹ Warshakoon, N.C.² Miller, M.J.³

50
- 34447514415
- (b) Kozikowski, A. P.; Park, P. J. Am. Chem. Soc. 1985, 107, 1736.
- (1985) Am. Chem. Soc , vol.107 , pp. 1736
- Kozikowski, A.P.¹ Park, P.J.²

51
- 0024994945
- (c) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668.
- (1990) J. Org. Chem , vol.55 , pp. 4668
- Kozikowski, A.P.¹ Park, P.²

52
- 0000702959
- (d) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 6115
- Flann, C.J.¹ Overman, L.E.²

53
- 0029962915
- (e) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 1054
- Yamada, H.¹ Aoyagi, S.² Kibayashi, C.³

54
- 0034616331
- (f) Huang, S.; Comins, D. L. Chem. Commun. 2000, 569.
- (2000) Chem. Commun , pp. 569
- Huang, S.¹ Comins, D.L.²

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