SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 21, Issue 10, 2014, Pages 3937-3941

A short scalable route to (-)-α-kainic acid using Pt-catalyzed direct allylic amination

(6) Zhang, Ming a Watanabe, Kenji a Tsukamoto, Masafumi a Shibuya, Ryozo a Morimoto, Hiroyuki a Ohshima, Takashi a,b

a KYUSHU UNIVERSITY (Japan)

b JAPAN SCIENCE AND TECHNOLOGY AGENCY (Japan)

Author keywords

Allylic amination; Amino acids; Homogeneous catalysis; Platinum; Total synthesis

Indexed keywords

AMINATION; AMINES; AMINO ACIDS; CATALYSIS; PLATINUM; SYNTHESIS (CHEMICAL);

ALLYLIC AMINATION; GRAM-SCALE SYNTHESIS; HOMOGENEOUS CATALYSIS; NATURAL PRODUCTS; NEUROPHARMACOLOGY; PHARMACEUTICAL AGENTS; SYNTHESIS FEATURES; TOTAL SYNTHESIS;

CYCLIZATION;

ALLYL COMPOUND; KAINIC ACID; PLATINUM;

AMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALLYL COMPOUNDS; AMINATION; CATALYSIS; CYCLIZATION; KAINIC ACID; MOLECULAR STRUCTURE; PLATINUM;

EID: 84943240426 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201406557 Document Type: Article

Times cited : (28)

References (64)

1
- 0042261072
- VCH, Weinheim
- K. C. Nicolaou, A. Snyder, Classics in Total Synthesis II: More Targets, Strategies, Methods, VCH, Weinheim, 2003.
- (2003) Classics in Total Synthesis II: More Targets, Strategies, Methods
- Nicolaou, K.C.¹ Snyder, A.²

2
- 84882907547
- a) L. Jorgensen, S. J. McKerrall, C. A. Kuttruff, F. Ungeheuer, J. Felding, P. S. Baran, Science 2013, 341, 878-882
- (2013) Science , vol.341 , pp. 878-882
- Jorgensen, L.¹ McKerrall, S.J.² Kuttruff, C.A.³ Ungeheuer, F.⁴ Felding, J.⁵ Baran, P.S.⁶

3
- 84891007243
- b) T. Mukaiyama, H. Ishikawa, H. Koshino, Y. Hayashi, Chem. Eur. J. 2013, 19, 17789-17800.
- (2013) Chem. Eur. J. , vol.19 , pp. 17789-17800
- Mukaiyama, T.¹ Ishikawa, H.² Koshino, H.³ Hayashi, Y.⁴

4
- 0001554750
- a) S. Murakami, T. Takemoto, Z. Shimizu, Yakugaku Zasshi 1953, 73, 1026-1028
- (1953) Yakugaku Zasshi , vol.73 , pp. 1026-1028
- Murakami, S.¹ Takemoto, T.² Shimizu, Z.³

5
- 0342848831
- b) H. Watase, Y. Tomie, I. Nitta, Bull. Chem. Soc. Jpn. 1958, 31, 714-725.
- (1958) Bull. Chem. Soc. Jpn. , vol.31 , pp. 714-725
- Watase, H.¹ Tomie, Y.² Nitta, I.³

6
- 0028087976
- S. Sakhi, A. Bruce, N. Sun, G. Tocco, M. Baudry, S. S. Schreiber, Proc. Natl. Acad. Sci. USA 1994, 91, 7525-7529.
- (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 7525-7529
- Sakhi, S.¹ Bruce, A.² Sun, N.³ Tocco, G.⁴ Baudry, M.⁵ Schreiber, S.S.⁶

7
- 66649137427
- R. Pietri, A. Lewis, R. G. Leon, G. Casabona, L. Kiger, S.-R. Yeh, S. Fernan-dez-Alberti, M. C. Marden, C. L. Cadilla, J. Lopez-Garriga, Biochemistry 2009, 48, 4881-4894.
- (2009) Biochemistry , vol.48 , pp. 4881-4894
- Pietri, R.¹ Lewis, A.² Leon, R.G.³ Casabona, G.⁴ Kiger, L.⁵ Yeh, S.-R.⁶ Fernan-Dez-Alberti, S.⁷ Marden, M.C.⁸ Cadilla, C.L.⁹ Lopez-Garriga, J.¹⁰

8
- 0022397573
- J. W. Geddes, D. T. Monaghan, C. W. Cotman, I.T. Lott, R. C. Kim, H. C. Chui, Science 1985, 230, 1179-1181.
- (1985) Science , vol.230 , pp. 1179-1181
- Geddes, J.W.¹ Monaghan, D.T.² Cotman, C.W.³ Lott, I.T.⁴ Kim, R.C.⁵ Chui, H.C.⁶

9
- 0017167057
- J. T. Coyle, R. Schwarcz, Nature 1976, 263, 244-246.
- (1976) Nature , vol.263 , pp. 244-246
- Coyle, J.T.¹ Schwarcz, R.²

10
- 84865312129
- C.I. Stathakis, E.G. Yioti, J. K. Gallos, Eur. J. Org. Chem. 2012, 4661-4673.
- (2012) Eur. J. Org. Chem. , pp. 4661-4673
- Stathakis, C.I.¹ Yioti, E.G.² Gallos, J.K.³

11
- 0000578889
- W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 4978-4979
- Oppolzer, W.¹ Thirring, K.²

12
- 0023272463
- a) J. Cooper, D.W. Knight, P. T. Gallagher, J. Chem. Soc. Chem. Commun. 1987, 1220-1222
- (1987) J. Chem. Soc. Chem. Commun. , pp. 1220-1222
- Cooper, J.¹ Knight, D.W.² Gallagher, P.T.³

13
- 0023679088
- b) S. Takano, Y. Iwabuchi, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1988, 1204-1206
- (1988) J. Chem. Soc. Chem. Commun. , pp. 1204-1206
- Takano, S.¹ Iwabuchi, Y.² Ogasawara, K.³

14
- 0023693459
- c) S. Takano, T. Sugihara, S. Satoh, K. Ogasawara, J. Am. Chem. Soc. 1988, 110, 6467-6471
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 6467-6471
- Takano, S.¹ Sugihara, T.² Satoh, S.³ Ogasawara, K.⁴

15
- 0025123660
- d) J. E. Baldwin, M. G. Moloney, A. F. Parsons, Tetrahedron 1990, 46, 7263-7282
- (1990) Tetrahedron , vol.46 , pp. 7263-7282
- Baldwin, J.E.¹ Moloney, M.G.² Parsons, A.F.³

16
- 37049072532
- e) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169-170
- (1992) J. Chem. Soc. Chem. Commun. , pp. 169-170
- Takano, S.¹ Inomata, K.² Ogasawara, K.³

17
- 37049082226
- f) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127
- (1993) J. Chem. Soc. Chem. Commun. , pp. 125-127
- Hatakeyama, S.¹ Sugawara, K.² Takano, S.³

18
- 0027300216
- g) S. e. Yoo, S. H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435-3438
- (1993) Tetrahedron Lett. , vol.34 , pp. 3435-3438
- Yoo, S.E.¹ Lee, S.H.² Jeong, N.³ Cho, I.⁴

19
- 0028044121
- h) S.-e. Yoo, S. H. Lee, J. Org. Chem. 1994, 59, 6968-6972
- (1994) J. Org. Chem. , vol.59 , pp. 6968-6972
- Yoo, S.-E.¹ Lee, S.H.²

20
- 0029767411
- i) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424
- (1996) J. Org. Chem. , vol.61 , pp. 5418-5424
- Hanessian, S.¹ Ninkovic, S.²

21
- 0001164390
- j) M. D. Bachi, A. Melman, J. Org. Chem. 1997, 62, 1896-1898
- (1997) J. Org. Chem. , vol.62 , pp. 1896-1898
- Bachi, M.D.¹ Melman, A.²

22
- 0001688764
- k) O. Miyata, Y. Ozawa, I. Ninomiya, T. Naito, Synlett 1997, 275-276
- (1997) Synlett , pp. 275-276
- Miyata, O.¹ Ozawa, Y.² Ninomiya, I.³ Naito, T.⁴

23
- 0031025516
- l) Y. Nakada, T. Sugahara, K. Ogasawara, Tetrahedron Lett. 1997, 38, 857-860
- (1997) Tetrahedron Lett. , vol.38 , pp. 857-860
- Nakada, Y.¹ Sugahara, T.² Ogasawara, K.³

24
- 0032499029
- m) A. Rubio, J. Ezquerra, A. Escribano, M. J. Remuinan, J. J. Vaquero, Tetrahedron Lett. 1998, 39, 2171-2174
- (1998) Tetrahedron Lett. , vol.39 , pp. 2171-2174
- Rubio, A.¹ Ezquerra, J.² Escribano, A.³ Remuinan, M.J.⁴ Vaquero, J.J.⁵

25
- 0033531354
- n) A. D. Campbell, T. M. Raynham, R. J. K. Taylor, Chem. Commun. 1999, 245-246
- (1999) Chem. Commun. , pp. 245-246
- Campbell, A.D.¹ Raynham, T.M.² Taylor, R.J.K.³

26
- 0033537060
- o) M. V. Chev-liakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139-11143
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11139-11143
- Chev-Liakov, M.V.¹ Montgomery, J.²

27
- 0033532090
- p) J. Cossy, M. Cases, D. G. Pardo, Tetrahedron 1999, 55, 6153-6166
- (1999) Tetrahedron , vol.55 , pp. 6153-6166
- Cossy, J.¹ Cases, M.² Pardo, D.G.³

28
- 0034619268
- q) A. D. Campbell, T. M. Raynham, R. J. K. Taylor, Perkin 1 2000, 3194-3204
- (2000) Perkin , vol.1 , pp. 3194-3204
- Campbell, A.D.¹ Raynham, T.M.² Taylor, R.J.K.³

29
- 0034682862
- r) O. Miyata, Y. Ozawa, I. Ninomiya, T. Naito, Tetrahedron 2000, 56, 6199-6207
- (2000) Tetrahedron , vol.56 , pp. 6199-6207
- Miyata, O.¹ Ozawa, Y.² Ninomiya, I.³ Naito, T.⁴

30
- 0034609677
- s) H. Nakagawa, T. Sugahara, K. Ogasawara, Org. Lett. 2000, 2, 3181-3183
- (2000) Org. Lett. , vol.2 , pp. 3181-3183
- Nakagawa, H.¹ Sugahara, T.² Ogasawara, K.³

31
- 0035825751
- t) Q. Xia, B. Ganem, Org. Lett. 2001, 3, 485-487
- (2001) Org. Lett. , vol.3 , pp. 485-487
- Xia, Q.¹ Ganem, B.²

32
- 0037013957
- u) J. Clay-den, C.J. Menet, K. Tchabanenko, Tetrahedron 2002, 58, 4727-4733
- (2002) Tetrahedron , vol.58 , pp. 4727-4733
- Clay-Den, J.¹ Menet, C.J.² Tchabanenko, K.³

33
- 7044241215
- v) M. M. Martinez, D. Hoppe, Org. Lett. 2004, 6, 3743-3746
- (2004) Org. Lett. , vol.6 , pp. 3743-3746
- Martinez, M.M.¹ Hoppe, D.²

34
- 23844545959
- w) J. C. Anderson, J. M. A. O'Loughlin, J. A. Tornos, Org. Biomol. Chem. 2005, 3, 2741-2749
- (2005) Org. Biomol. Chem. , vol.3 , pp. 2741-2749
- Anderson, J.C.¹ O'Loughlin, J.M.A.² Tornos, J.A.³

35
- 16444381572
- x) M. M. Martinez, D. Hoppe, Eur. J. Org. Chem. 2005, 1427-1443
- (2005) Eur. J. Org. Chem. , pp. 1427-1443
- Martinez, M.M.¹ Hoppe, D.²

36
- 29944432210
- y) J.-F. Poisson, A. Orellana, A. E. Greene, J. Org. Chem. 2005, 70, 10860-10863
- (2005) J. Org. Chem. , vol.70 , pp. 10860-10863
- Poisson, J.-F.¹ Orellana, A.² Greene, A.E.³

37
- 22244472986
- z) M. E. Scott, M. Lautens, Org. Lett. 2005, 7, 3045-3047
- (2005) Org. Lett. , vol.7 , pp. 3045-3047
- Scott, M.E.¹ Lautens, M.²

38
- 34848876647
- aa) J. M. Chalker, A. Yang, K. Deng, T. Cohen, Org. Lett. 2007, 9, 3825-3828
- (2007) Org. Lett. , vol.9 , pp. 3825-3828
- Chalker, J.M.¹ Yang, A.² Deng, K.³ Cohen, T.⁴

39
- 37549008781
- ab) Y. C. Jung, C. H. Yoon, E. Turos, K. S. Yoo, K. W. Jung, J. Org. Chem. 2007, 72, 10114-10122
- (2007) J. Org. Chem. , vol.72 , pp. 10114-10122
- Jung, Y.C.¹ Yoon, C.H.² Turos, E.³ Yoo, K.S.⁴ Jung, K.W.⁵

40
- 34248387352
- ac) H. Sakaguchi, H. Tokuyama, T. Fu-kuyama, Org. Lett. 2007, 9, 1635-1638
- (2007) Org. Lett. , vol.9 , pp. 1635-1638
- Sakaguchi, H.¹ Tokuyama, H.² Fu-Kuyama, T.³

41
- 48849098730
- ad) H. Sakaguchi, H. Tokuyama, T. Fukuyama, Org. Lett. 2008, 10, 1711-1714
- (2008) Org. Lett. , vol.10 , pp. 1711-1714
- Sakaguchi, H.¹ Tokuyama, H.² Fukuyama, T.³

42
- 51549087097
- ae) K. Tomooka, T. Akiya-ma, P. Man, M. Suzuki, Tetrahedron Lett. 2008, 49, 6327-6329
- (2008) Tetrahedron Lett. , vol.49 , pp. 6327-6329
- Tomooka, K.¹ Akiya-Ma, T.² Man, P.³ Suzuki, M.⁴

43
- 77749298192
- af) A. Far-wick, G. Helmchen, Org. Lett. 2010, 12, 1108-1111
- (2010) Org. Lett. , vol.12 , pp. 1108-1111
- Far-Wick, A.¹ Helmchen, G.²

44
- 78650413655
- ag) K. Kitamoto, M. Sampei, Y. Nakayama, T. Sato, N. Chida, Org. Lett. 2010, 12, 5756-5759
- (2010) Org. Lett. , vol.12 , pp. 5756-5759
- Kitamoto, K.¹ Sampei, M.² Nakayama, Y.³ Sato, T.⁴ Chida, N.⁵

45
- 79951827490
- ah) A. Farwick, J. U. Engelhart, O. Tverskoy, C. Welter, Q. A. Umlauf, F. Ro-minger, W. J. Kerr, G. Helmchen, Adv. Synth. Catal. 2011, 353, 349-370
- (2011) Adv. Synth. Catal. , vol.353 , pp. 349-370
- Farwick, A.¹ Engelhart, J.U.² Tverskoy, O.³ Welter, C.⁴ Umlauf, Q.A.⁵ Ro-Minger, F.⁶ Kerr, W.J.⁷ Helmchen, G.⁸

46
- 79955414500
- ai) S. Takita, S. Yokoshima, T. Fukuyama, Org. Lett. 2011, 13, 2068-2070
- (2011) Org. Lett. , vol.13 , pp. 2068-2070
- Takita, S.¹ Yokoshima, S.² Fukuyama, T.³

47
- 84857755116
- aj) P. A. Evans, P. A. Inglesby, J. Am. Chem. Soc. 2012, 134, 3635-3638
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 3635-3638
- Evans, P.A.¹ Inglesby, P.A.²

48
- 84864215190
- ak) K. Kitamoto, Y. Nakayama, M. Sampei, M. Ichiki, N. Furuya, T. Sato, N. Chida, Eur. J. Org. Chem. 2012, 4217-4231
- (2012) Eur. J. Org. Chem. , pp. 4217-4231
- Kitamoto, K.¹ Nakayama, Y.² Sampei, M.³ Ichiki, M.⁴ Furuya, N.⁵ Sato, T.⁶ Chida, N.⁷

49
- 84862076988
- al) Z. Luo, B. Zhou, Y. Li, Org. Lett. 2012, 14, 2540-2543
- (2012) Org. Lett. , vol.14 , pp. 2540-2543
- Luo, Z.¹ Zhou, B.² Li, Y.³

50
- 84862564460
- am) A. Orellana, S. K. Pandey, S. Carret, A. E. Greene, J.-F. Poisson, J. Org. Chem. 2012, 77, 5286-5296
- (2012) J. Org. Chem. , vol.77 , pp. 5286-5296
- Orellana, A.¹ Pandey, S.K.² Carret, S.³ Greene, A.E.⁴ Poisson, J.-F.⁵

51
- 84867229020
- an) H.-J. Yu, C. Shao, Z. Cui, C.-G. Feng, G.-Q. Lin, Chem. Eur. J. 2012, 18, 13274-13278
- (2012) Chem. Eur. J. , vol.18 , pp. 13274-13278
- Yu, H.-J.¹ Shao, C.² Cui, Z.³ Feng, C.-G.⁴ Lin, G.-Q.⁵

52
- 84875962403
- ao) N. Kesava Reddy, S. Chandrasekhar, J. Org. Chem. 2013, 78, 3355-3360
- (2013) J. Org. Chem. , vol.78 , pp. 3355-3360
- Kesava Reddy, N.¹ Chandrasekhar, S.²

53
- 84899873403
- ap) K. Oe, Y. Ohfune, T. Shinada, Org. Lett. 2014, 16, 2550-2553.
- (2014) Org. Lett. , vol.16 , pp. 2550-2553
- Oe, K.¹ Ohfune, Y.² Shinada, T.³

54
- 34548175723
- a) M. Utsunomiya, Y. Miyamoto, J. Ipposhi, T. Ohshima, K. Mashima, Org. Lett. 2007, 9, 3371-3374
- (2007) Org. Lett. , vol.9 , pp. 3371-3374
- Utsunomiya, M.¹ Miyamoto, Y.² Ipposhi, J.³ Ohshima, T.⁴ Mashima, K.⁵

55
- 70349919537
- b) T. Ohshima, Y. Miyamoto, J. Ipposhi, Y. Na-kahara, M. Utsunomiya, K. Mashima, J. Am. Chem. Soc. 2009, 131, 14317-14328
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 14317-14328
- Ohshima, T.¹ Miyamoto, Y.² Ipposhi, J.³ Na-Kahara, Y.⁴ Utsunomiya, M.⁵ Mashima, K.⁶

56
- 84855283908
- c) K. Das, R. Shibuya, Y. Nakahara, N. Germain, T. Ohshi-ma, K. Mashima, Angew. Chem. Int. Ed. 2012, 51, 150-154
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 150-154
- Das, K.¹ Shibuya, R.² Nakahara, Y.³ Germain, N.⁴ Ohshi-Ma, T.⁵ Mashima, K.⁶

57
- 84865068826
- Angew. Chem. 2012, 124, 154-158
- (2012) Angew. Chem. , vol.124 , pp. 154-158

58
- 84899024176
- d) R. Shibuya, L. Lin, Y. Nakahara, K. Mashi-ma, T. Ohshima, Angew. Chem. Int. Ed. 2014, 53, 4377-4381
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4377-4381
- Shibuya, R.¹ Lin, L.² Nakahara, Y.³ Mashi-Ma, K.⁴ Ohshima, T.⁵

59
- 84943269662
- Angew. Chem. 2014, 126, 4466-4470.
- (2014) Angew. Chem. , vol.126 , pp. 4466-4470

60
- 0001475361
- T. Tsuda, Y. Horii, Y. Nakagawa, T. Ishida, T. Saegusa, J. Org. Chem. 1989, 54, 977-979.
- (1989) J. Org. Chem. , vol.54 , pp. 977-979
- Tsuda, T.¹ Horii, Y.² Nakagawa, Y.³ Ishida, T.⁴ Saegusa, T.⁵

61
- 79953701945
- a) C. Vaxelaire, P. Winter, M. Christmann, Angew. Chem. Int. Ed. 2011, 50, 3605-3607
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 3605-3607
- Vaxelaire, C.¹ Winter, P.² Christmann, M.³

62
- 80052495979
- Angew. Chem. 2011, 123, 3685-3687
- (2011) Angew. Chem. , vol.123 , pp. 3685-3687

63
- 84875193245
- b) Y. Hayashi, S. Ume-miya, Angew. Chem. Int. Ed. 2013, 52, 3450-3452
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 3450-3452
- Hayashi, Y.¹ Ume-Miya, S.²

64
- 84890790479
- Angew. Chem. 2013, 125, 3534-3536.
- (2013) Angew. Chem. , vol.125 , pp. 3534-3536

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.