SCOPUS 정보 검색 플랫폼

Volumn 1996, Issue 1, 1996, Pages 39-42

Diastereoselective Synthesis of Pyrrolidines by 5-Exo-trig Cyclizations of α-Amino Radicals Derived from N-(α-Benzotriazolylalkyl)alkenylamines and Samarium Diiodide

(2) Aurrecoechea, José M a Fernández Acebes, Alvaro a

a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013575961 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-1996-5316 Document Type: Article

Times cited : (15)

References (52)

1
- 0028045316
- For some recent references see: Wang, Y. F.; Takaoka, Y.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Yang, T. K.; Yeh, S. T.; Lay, Y. Y. Heterocycles 1994, 38, 1711. Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456. Plunkett, A. O. Nat. Prod. Rep. 1994, 11 581 . Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
- (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1242
- Wang, Y.F.¹ Takaoka, Y.² Wong, C.H.³

2
- 1242268700
- For some recent references see: Wang, Y. F.; Takaoka, Y.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Yang, T. K.; Yeh, S. T.; Lay, Y. Y. Heterocycles 1994, 38, 1711. Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456. Plunkett, A. O. Nat. Prod. Rep. 1994, 11 581 . Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
- (1994) Heterocycles , vol.38 , pp. 1711
- Yang, T.K.¹ Yeh, S.T.² Lay, Y.Y.³

3
- 0028357496
- For some recent references see: Wang, Y. F.; Takaoka, Y.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Yang, T. K.; Yeh, S. T.; Lay, Y. Y. Heterocycles 1994, 38, 1711. Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456. Plunkett, A. O. Nat. Prod. Rep. 1994, 11 581 . Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
- (1994) J. Org. Chem. , vol.59 , pp. 2456
- Artis, D.R.¹ Cho, I.S.² Jaime-Figueroa, S.³ Muchowski, J.M.⁴

4
- 0028312466
- For some recent references see: Wang, Y. F.; Takaoka, Y.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Yang, T. K.; Yeh, S. T.; Lay, Y. Y. Heterocycles 1994, 38, 1711. Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456. Plunkett, A. O. Nat. Prod. Rep. 1994, 11 581 . Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
- (1994) Nat. Prod. Rep. , vol.11 , pp. 581
- Plunkett, A.O.¹

5
- 0027979680
- For some recent references see: Wang, Y. F.; Takaoka, Y.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Yang, T. K.; Yeh, S. T.; Lay, Y. Y. Heterocycles 1994, 38, 1711. Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456. Plunkett, A. O. Nat. Prod. Rep. 1994, 11 581 . Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
- (1994) Tetrahedron , vol.50 , pp. 1033
- Farr, R.A.¹ Holland, A.K.² Huber, E.W.³ Peet, N.P.⁴ Weintraub, P.M.⁵

6
- 0001567161
- For some recent references see: Wang, Y. F.; Takaoka, Y.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Yang, T. K.; Yeh, S. T.; Lay, Y. Y. Heterocycles 1994, 38, 1711. Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456. Plunkett, A. O. Nat. Prod. Rep. 1994, 11 581 . Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
- (1995) J. Org. Chem. , vol.60 , pp. 103
- Ryu, Y.¹ Kim, G.²

7
- 0000709398
- For a survey of commonly encountered strategies see: Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1993, 58, 3857.
- (1993) J. Org. Chem. , vol.58 , pp. 3857
- Denmark, S.E.¹ Marcin, L.R.²

8
- 15044342910
- A. R. Katritzky, Ed.; Academic Press: San Diego
- For a review on the use of nitrogen-centered radicals see: Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry, Vol 58; A. R. Katritzky, Ed.; Academic Press: San Diego, 1993; Vol. 58; p 1.
- (1993) Advances in Heterocyclic Chemistry, Vol 58 , vol.58 , pp. 1
- Esker, J.L.¹ Newcomb, M.²

9
- 85064667006
- Curran, D. P. Synthesis 1988, 417; 489. Jaspersc, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
- (1988) Synthesis , vol.417 , pp. 489
- Curran, D.P.¹

10
- 0000702878
- Curran, D. P. Synthesis 1988, 417; 489. Jaspersc, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
- (1991) Chem. Rev. , vol.91 , pp. 1237
- Jaspersc, C.P.¹ Curran, D.P.² Fevig, T.L.³

11
- 0010330514
- Tokuda, M.; Fujita, H.; Suginome, H. J. Chem. Soc., Perkin Trans. 1 1994, 777.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 777
- Tokuda, M.¹ Fujita, H.² Suginome, H.³

12
- 0028348460
- Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1745.
- (1994) Tetrahedron , vol.50 , pp. 1745
- Boivin, J.¹ Fouquet, E.² Zard, S.Z.³

13
- 0001496128
- Esker, J. L.; Newcomb, M. J. Org. Chem. 1993, 58, 4933. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779.
- (1993) J. Org. Chem. , vol.58 , pp. 4933
- Esker, J.L.¹ Newcomb, M.²

14
- 0000200802
- Esker, J. L.; Newcomb, M. J. Org. Chem. 1993, 58, 4933. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779.
- (1994) J. Org. Chem. , vol.59 , pp. 2779
- Esker, J.L.¹ Newcomb, M.²

15
- 0022409073
- Choi, J. K.; Hart, D. J. Tetrahedron 1985, 41, 3959.
- (1985) Tetrahedron , vol.41 , pp. 3959
- Choi, J.K.¹ Hart, D.J.²

16
- 1542572036
- Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233.
- (1992) Acc. Chem. Res. , vol.25 , pp. 233
- Yoon, U.C.¹ Mariano, P.S.²

17
- 0000874522
- Bachi, M. D.; Balanov, A.; Barner, N. J. Org. Chem. 1994, 59, 7752.
- (1994) J. Org. Chem. , vol.59 , pp. 7752
- Bachi, M.D.¹ Balanov, A.² Barner, N.³

18
- 0026633735
- Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907.
- (1992) Tetrahedron , vol.48 , pp. 4659
- Esch, P.M.¹ Hiemstra, H.² De Boer, R.F.³ Speckamp, W.N.⁴

19
- 0028355342
- Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907.
- (1994) Tetrahedron , vol.50 , pp. 1907
- Udding, J.H.¹ Tuijp, C.J.M.² Hiemstra, H.³ Speckamp, W.N.⁴

20
- 0026630367
- Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Parsons, A. F.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 1945. Knochel, P. Synlett 1995, 393.
- (1992) Tetrahedron , vol.48 , pp. 9373
- Baldwin, J.E.¹ Moloney, M.G.² Parsons, A.F.³

21
- 37049071059
- Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Parsons, A. F.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 1945. Knochel, P. Synlett 1995, 393.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1945
- Parsons, A.F.¹ Taylor, R.J.K.²

22
- 0003170224
- Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Parsons, A. F.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 1945. Knochel, P. Synlett 1995, 393.
- (1995) Synlett , pp. 393
- Knochel, P.¹

23
- 37049085339
- Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1994, 455; 1383.
- (1994) J. Chem. Soc., Chem. Commun. , vol.455 , pp. 1383
- Yuasa, Y.¹ Ando, J.² Shibuya, S.³

24
- 0003444932
- A. G. Cook, Ed.; Marcel Dekker: New York
- Paukstelis, J. V.; Cook, A. G. In Enamines. Synthesis, Structure and Reactions; 2nd ed.; A. G. Cook, Ed.; Marcel Dekker: New York, 1988; p 275.
- (1988) Enamines. Synthesis, Structure and Reactions; 2nd Ed. , pp. 275
- Paukstelis, J.V.¹ Cook, A.G.²

25
- 45549111181
- Martin, S. F.; Yang, C. P.; Laswell, W. L.; Rüeger, H. Tetrahedron Lett. 1988, 29, 6685.
- (1988) Tetrahedron Lett. , vol.29 , pp. 6685
- Martin, S.F.¹ Yang, C.P.² Laswell, W.L.³ Rüeger, H.⁴

26
- 0010077452
- For recent reviews see: (a) Molander, G. A. Chem. Rev. 1992, 92, 29. (b) Molander, G. A. In Organic Reactions, Vol 46; L. A. Raquette, Ed.; John Wiley & Sons, 1994; p 211.
- (1992) Chem. Rev. , vol.92 , pp. 29
- Molander, G.A.¹

27
- 0001367782
- L. A. Raquette, Ed.; John Wiley & Sons
- For recent reviews see: (a) Molander, G. A. Chem. Rev. 1992, 92, 29. (b) Molander, G. A. In Organic Reactions, Vol 46; L. A. Raquette, Ed.; John Wiley & Sons, 1994; p 211.
- (1994) Organic Reactions , vol.46 , pp. 211
- Molander, G.A.¹

28
- 0027507069
- Aurrecoechea, J. M.; Fernández-Acebes, A. Tetrahedron Lett. 1993, 34, 549.
- (1993) Tetrahedron Lett. , vol.34 , pp. 549
- Aurrecoechea, J.M.¹ Fernández-Acebes, A.²

29
- 0001117210
- 2-mediated radical ring-closures see: Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729. Shiue, J. S.; Fang, J. M. J. Chem. Soc. Chem. Commun. 1993, 1277. Baldwin, J. E.; Mackenzieturner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9411; 9425.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 8729
- Ogawa, A.¹ Takami, N.² Sekiguchi, M.³ Ryu, I.⁴ Kambe, N.⁵ Sonoda, N.⁶

30
- 1542377045
- 2-mediated radical ring-closures see: Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729. Shiue, J. S.; Fang, J. M. J. Chem. Soc. Chem. Commun. 1993, 1277. Baldwin, J. E.; Mackenzieturner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9411; 9425.
- (1993) J. Chem. Soc. Chem. Commun. , pp. 1277
- Shiue, J.S.¹ Fang, J.M.²

31
- 0028129634
- 2-mediated radical ring-closures see: Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729. Shiue, J. S.; Fang, J. M. J. Chem. Soc. Chem. Commun. 1993, 1277. Baldwin, J. E.; Mackenzieturner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9411; 9425.
- (1994) Tetrahedron , vol.50 , pp. 9411
- Baldwin, J.E.¹ Mackenzieturner, S.C.² Moloney, M.G.³

32
- 85033741209
- note
- 2: 309.17288, found 309.17273.

33
- 0000279109
- The starting amines 2-4 were known compounds, Amine 3: Brandmaster, S. M.; Ojima, I. Tetrahedron Lett. 1987, 28, 613. Amines 2,4: Brands, K. M. J.; Meekel, A. A. P.; Pandit, U. K. Tetrahedron 1991, 47, 2005.
- (1987) Tetrahedron Lett. , vol.28 , pp. 613
- Brandmaster, S.M.¹ Ojima, I.²

34
- 0026022048
- The starting amines 2-4 were known compounds, Amine 3: Brandmaster, S. M.; Ojima, I. Tetrahedron Lett. 1987, 28, 613. Amines 2,4: Brands, K. M. J.; Meekel, A. A. P.; Pandit, U. K. Tetrahedron 1991, 47, 2005.
- (1991) Tetrahedron , vol.47 , pp. 2005
- Brands, K.M.J.¹ Meekel, A.A.P.² Pandit, U.K.³

35
- 37049083296
- They easily revert to the starting amine and aldehyde in the presence of water and traces of acid: Katritzky, A. R.; Yannakopoulou, K.; Lue, P.; Rasala, D.; Urogdi, L. J. Chem. Soc., Perkin Trans. 1 1989, 225.
- (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 225
- Katritzky, A.R.¹ Yannakopoulou, K.² Lue, P.³ Rasala, D.⁴ Urogdi, L.⁵

36
- 37049089602
- Katritzky, A. R.; Yannakapoulou, K.; Kuzmierkiewicz, W.; Aurrecoechca, J. M.; Palenik, G. J.; Koziol, A. E.; Szczesniak, M.; Skarjune, R. J. Chem. Soc., Perkin Trans. 1 1987, 2673.
- (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 2673
- Katritzky, A.R.¹ Yannakapoulou, K.² Kuzmierkiewicz, W.³ Aurrecoechca, J.M.⁴ Palenik, G.J.⁵ Koziol, A.E.⁶ Szczesniak, M.⁷ Skarjune, R.⁸

37
- 0026739672
- Aurrecoechea, J. M.; Fernández,-Acebes, A. Tetrahedron Lett. 1992, 33, 4763.
- (1992) Tetrahedron Lett. , vol.33 , pp. 4763
- Aurrecoechea, J.M.¹ Fernández-Acebes, A.²

38
- 0000221903
- Padwa, A.; Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620. Padwa, A.; Dent, W.; Nimmesgern, H.; Venkatramanan, M. K.; Wong, G. S. K. Chem. Ber. 1986, 119, 813.
- (1985) J. Org. Chem. , vol.50 , pp. 5620
- Padwa, A.¹ Nimmesgern, H.² Wong, G.S.K.³

39
- 84982687934
- Padwa, A.; Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620. Padwa, A.; Dent, W.; Nimmesgern, H.; Venkatramanan, M. K.; Wong, G. S. K. Chem. Ber. 1986, 119, 813.
- (1986) Chem. Ber. , vol.119 , pp. 813
- Padwa, A.¹ Dent, W.² Nimmesgern, H.³ Venkatramanan, M.K.⁴ Wong, G.S.K.⁵

40
- 0024502584
- Choi, J. K.; Ha, D. C.; Hart, D. J.; Lee, C. S.; Ramesh, S.; Wu, S. J. Org. Chem. 1989, 54, 279.
- (1989) J. Org. Chem. , vol.54 , pp. 279
- Choi, J.K.¹ Ha, D.C.² Hart, D.J.³ Lee, C.S.⁴ Ramesh, S.⁵ Wu, S.⁶

41
- 0042144986
- Pasto, D. J.; Krasnanski, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062.
- (1987) J. Org. Chem. , vol.52 , pp. 3062
- Pasto, D.J.¹ Krasnanski, R.² Zercher, C.³

42
- 77956723367
- Sustmann, R.; Korth, H. G. Adv. Phys. Org. Chem. 1990, 26, 131.
- (1990) Adv. Phys. Org. Chem. , vol.26 , pp. 131
- Sustmann, R.¹ Korth, H.G.²

43
- 0003391885
- Chapman and Hall: London
- Whitesell, J. K.; Minton, M. A. Stereochemical Analysis of Alycyclic Compounds by C-13 NMR Spectroscopy; Chapman and Hall: London, 1987.
- (1987) Stereochemical Analysis of Alycyclic Compounds by C-13 NMR Spectroscopy
- Whitesell, J.K.¹ Minton, M.A.²

44
- 85033750445
- Doctoral Thesis, Universidad del País Vasco
- Fernández-Acebes, A. Doctoral Thesis, Universidad del País Vasco, 1995.
- (1995)
- Fernández-Acebes, A.¹

45
- 85033757261
- note
- 32 have been reported. We thank a referee for calling these points to our attention.

46
- 0000892265
- Murakami, M.; Hayashi, M.; Ito, Y. J. Org. Chem. 1992, 57, 793. Collin, J.; Namy, J. L.; Jones, G.; Kagan, H. B. Tetrahedron Lett. 1992, 33, 2973. Booth, S. E.; Benneche, T.; Undheim, K. Tetrahedron 1995, 51, 3665.
- (1992) J. Org. Chem. , vol.57 , pp. 793
- Murakami, M.¹ Hayashi, M.² Ito, Y.³

47
- 0026636846
- Murakami, M.; Hayashi, M.; Ito, Y. J. Org. Chem. 1992, 57, 793. Collin, J.; Namy, J. L.; Jones, G.; Kagan, H. B. Tetrahedron Lett. 1992, 33, 2973. Booth, S. E.; Benneche, T.; Undheim, K. Tetrahedron 1995, 51, 3665.
- (1992) Tetrahedron Lett. , vol.33 , pp. 2973
- Collin, J.¹ Namy, J.L.² Jones, G.³ Kagan, H.B.⁴

48
- 0028930169
- Murakami, M.; Hayashi, M.; Ito, Y. J. Org. Chem. 1992, 57, 793. Collin, J.; Namy, J. L.; Jones, G.; Kagan, H. B. Tetrahedron Lett. 1992, 33, 2973. Booth, S. E.; Benneche, T.; Undheim, K. Tetrahedron 1995, 51, 3665.
- (1995) Tetrahedron , vol.51 , pp. 3665
- Booth, S.E.¹ Benneche, T.² Undheim, K.³

49
- 0010530025
- Curran, D. P.; Wolin, R. L. Synlett 1991, 317.
- (1991) Synlett , pp. 317
- Curran, D.P.¹ Wolin, R.L.²

50
- 0000020896
- Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. M. J. Org. Chem. 1987, 52, 959. Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143.
- (1985) Tetrahedron , vol.41 , pp. 3925
- Beckwith, A.L.J.¹ Schiesser, C.H.²

51
- 33845282341
- Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. M. J. Org. Chem. 1987, 52, 959. Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143.
- (1987) J. Org. Chem. , vol.52 , pp. 959
- Spellmeyer, D.C.¹ Houk, K.M.²

52
- 0000799645
- Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. M. J. Org. Chem. 1987, 52, 959. Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143.
- (1993) Chem. Soc. Rev. , vol.22 , pp. 143
- Beckwith, A.L.J.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.