SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 22, 2013, Pages 5818-5821

Highly stereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with methyl (diazoacetoxy)acetate catalyzed by a chiral ruthenium(II) complex

(4) Chanthamath, Soda a Takaki, Suguru a Shibatomi, Kazutaka a Iwasa, Seiji a

a TOYOHASHI UNIVERSITY OF TECHNOLOGY (Japan)

Author keywords

, unsaturated carbonyl compounds; asymmetric cyclopropanation; carbenes; methyl (diazoacetoxy)acetate; ruthenium

Indexed keywords

ASYMMETRIC CYCLOPROPANATION; CARBENES; CYCLOPROPANATION; ENANTIOSELECTIVE TOTAL SYNTHESIS; METHYL (DIAZOACETOXY)ACETATE; NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS; RUTHENIUM COMPLEXES; UNSATURATED CARBONYL COMPOUNDS;

CARBONYL COMPOUNDS; PROPANE; REACTION INTERMEDIATES; RUTHENIUM; STEREOSELECTIVITY; VOLATILE FATTY ACIDS;

RUTHENIUM COMPOUNDS;

AZO COMPOUND; COORDINATION COMPOUND; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AZO COMPOUNDS; CATALYSIS; COORDINATION COMPLEXES; CYCLIZATION; CYCLOPROPANES; MOLECULAR STRUCTURE; REVERSE TRANSCRIPTASE INHIBITORS; RUTHENIUM; STEREOISOMERISM;

EID: 84878056790 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201300468 Document Type: Article

Times cited : (51)

References (61)

1
- 0035828834
- W. A. Donaldson, Tetrahedron 2001, 57, 8589-8627
- (2001) Tetrahedron , vol.57 , pp. 8589-8627
- Donaldson, W.A.¹

2
- 0038301324
- J. Pietruszka, Chem. Rev. 2003, 103, 1051-1070
- (2003) Chem. Rev. , vol.103 , pp. 1051-1070
- Pietruszka, J.¹

3
- 0038561146
- L. A. Wessjohann, W. Brandt, T. Thiemann, Chem. Rev. 2003, 103, 1625-1647
- (2003) Chem. Rev. , vol.103 , pp. 1625-1647
- Wessjohann, L.A.¹ Brandt, W.² Thiemann, T.³

4
- 0038222536
- H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. J. Charette, Chem. Rev. 2003, 103, 977-1050
- (2003) Chem. Rev. , vol.103 , pp. 977-1050
- Lebel, H.¹ Marcoux, J.-F.² Molinaro, C.³ Charette, A.B.J.⁴

5
- 1642265747
- A. Armstrong, J. N. Scutt, Chem. Commun. 2004, 510-511
- (2004) Chem. Commun. , pp. 510-511
- Armstrong, A.¹ Scutt, J.N.²

6
- 45649083650
- H. Pellissier, Tetrahedron 2008, 64, 7041-7095
- (2008) Tetrahedron , vol.64 , pp. 7041-7095
- Pellissier, H.¹

7
- 84862583428
- D. Y.-K. Chen, R. H. Pouwer, J.-A. Richard, Chem. Soc. Rev. 2012, 41, 4631-4642.
- (2012) Chem. Soc. Rev. , vol.41 , pp. 4631-4642
- Chen, D.Y.-K.¹ Pouwer, R.H.² Richard, J.-A.³

8
- 0025184973
- M. P. Doyle, B. D. Brandes, A. P. Kazala, R. J. Pieters, M. B. Jarstfer, L. M. Watkins, C. T. Eagle, Tetrahedron Lett. 1990, 31, 6613-6616
- (1990) Tetrahedron Lett. , vol.31 , pp. 6613-6616
- Doyle, M.P.¹ Brandes, B.D.² Kazala, A.P.³ Pieters, R.J.⁴ Jarstfer, M.B.⁵ Watkins, L.M.⁶ Eagle, C.T.⁷

9
- 0025042702
- R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008
- (1990) Tetrahedron Lett. , vol.31 , pp. 6005-6008
- Lowenthal, R.E.¹ Abiko, A.² Masamune, S.³

10
- 85008090337
- D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 726-728
- Evans, D.A.¹ Woerpel, K.A.² Hinman, M.M.³ Faul, M.M.⁴

11
- 0000139463
- H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 2223-2224
- Nishiyama, H.¹ Itoh, Y.² Matsumoto, H.³ Park, S.-B.⁴ Itoh, K.⁵

12
- 0000838994
- J. A. Miller, W. Jin, S. T. Nguyen, Angew. Chem. 2002, 114, 3077-3080
- (2002) Angew. Chem. , vol.114 , pp. 3077-3080
- Miller, J.A.¹ Jin, W.² Nguyen, S.T.³

13
- 0037119302
- Angew. Chem. Int. Ed. 2002, 41, 2953-2956
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2953-2956

14
- 29144482562
- M. Itagaki, Y. Yamamoto, Tetrahedron Lett. 2006, 47, 523-525
- (2006) Tetrahedron Lett. , vol.47 , pp. 523-525
- Itagaki, M.¹ Yamamoto, Y.²

15
- 35148831172
- V. D. M. Hoang, P. A. N. Reddy, T.-J. Kim, Tetrahedron Lett. 2007, 48, 8014-8017
- (2007) Tetrahedron Lett. , vol.48 , pp. 8014-8017
- Hoang, V.D.M.¹ Reddy, P.A.N.² Kim, T.-J.³

16
- 34547236674
- Y. Chen, X. P. Zhang, J. Org. Chem. 2007, 72, 5931-5934
- (2007) J. Org. Chem. , vol.72 , pp. 5931-5934
- Chen, Y.¹ Zhang, X.P.²

17
- 48749095700
- H. Suematsu, S. Kanchiku, T. Uchida, T. Katsuki, J. Am. Chem. Soc. 2008, 130, 10327-10337.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 10327-10337
- Suematsu, H.¹ Kanchiku, S.² Uchida, T.³ Katsuki, T.⁴

18
- 0142048804
- W. Kirmse, Angew. Chem. 2003, 115, 1120-1125
- (2003) Angew. Chem. , vol.115 , pp. 1120-1125
- Kirmse, W.¹

19
- 0037429821
- Angew. Chem. Int. Ed. 2003, 42, 1088-1093
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1088-1093

20
- 4644279024
- H. A. McManus, P. J. Guiry, Chem. Rev. 2004, 104, 4151-4202
- (2004) Chem. Rev. , vol.104 , pp. 4151-4202
- McManus, H.A.¹ Guiry, P.J.²

21
- 23044451983
- T. Portada, M. Roje, Z. Hamersak, M. Zinic, Tetrahedron Lett. 2005, 46, 5957-5959
- (2005) Tetrahedron Lett. , vol.46 , pp. 5957-5959
- Portada, T.¹ Roje, M.² Hamersak, Z.³ Zinic, M.⁴

22
- 33749828310
- G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561-3651
- (2006) Chem. Rev. , vol.106 , pp. 3561-3651
- Desimoni, G.¹ Faita, G.² Jørgensen, K.A.³

23
- 34250644975
- T. Portada, M. Roje, Z. Raza, V. Čaplar, M. Žinic̈, V. Šunjic̈, Eur. J. Org. Chem. 2007, 838-856.
- (2007) Eur. J. Org. Chem. , pp. 838-856
- Portada, T.¹ Roje, M.² Raza, Z.³ Čaplar, V.⁴ Žinic̈, M.⁵ Šunjic̈, V.⁶

24
- 0038345074
- M. P. Doyle, M. Yan, H.-M. Gau, E. C. Blossey, Org. Lett. 2003, 5, 561-563
- (2003) Org. Lett. , vol.5 , pp. 561-563
- Doyle, M.P.¹ Yan, M.² Gau, H.-M.³ Blossey, E.C.⁴

25
- 3242798105
- Y. Lou, M. Horikawa, R. A. Kloster, N. A. Hawryluk, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 8916-8918
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 8916-8918
- Lou, Y.¹ Horikawa, M.² Kloster, R.A.³ Hawryluk, N.A.⁴ Corey, E.J.⁵

26
- 20544445395
- P. Müller, G. Bernardinelli, Y. F. Allenbach, M. Ferri, S. Grass, Synlett 2005, 1397-1400
- (2005) Synlett , pp. 1397-1400
- Müller, P.¹ Bernardinelli, G.² Allenbach, Y.F.³ Ferri, M.⁴ Grass, S.⁵

27
- 22244464549
- H. M. L. Davies, A. M. Walji, Org. Lett. 2005, 7, 2941-2944
- (2005) Org. Lett. , vol.7 , pp. 2941-2944
- Davies, H.M.L.¹ Walji, A.M.²

28
- 33744462643
- P. Müller, G. Bernardinelli, Y. F. Allenbach, S. Chappellet, A. Ghanem, Synthesis 2006, 1689-1696.
- (2006) Synthesis , pp. 1689-1696
- Müller, P.¹ Bernardinelli, G.² Allenbach, Y.F.³ Chappellet, S.⁴ Ghanem, A.⁵

29
- 0142119412
- A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756
- (2003) Chem. Eur. J. , vol.9 , pp. 4746-4756
- Berkessel, A.¹ Kaiser, P.² Lex, J.³

30
- 0037418809
- S. Iwasa, S. Tsushima, K. Nishiyama, Y. Tsuchiya, F. Takezawa, H. Nishiyama, Tetrahedron: Asymmetry 2003, 14, 855-865
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 855-865
- Iwasa, S.¹ Tsushima, S.² Nishiyama, K.³ Tsuchiya, Y.⁴ Takezawa, F.⁵ Nishiyama, H.⁶

31
- 29244489022
- A. B. Charette, J.-E. Bouchard, Can. J. Chem. 2005, 83, 533-542
- (2005) Can. J. Chem. , vol.83 , pp. 533-542
- Charette, A.B.¹ Bouchard, J.-E.²

32
- 34247525837
- J. A. Miller, B. A. Gross, M. A. Zhuravel, W. Jin, S. T. Nguyen, Angew. Chem. 2005, 117, 3953-3957
- (2005) Angew. Chem. , vol.117 , pp. 3953-3957
- Miller, J.A.¹ Gross, B.A.² Zhuravel, M.A.³ Jin, W.⁴ Nguyen, S.T.⁵

33
- 21244474495
- Angew. Chem. Int. Ed. 2005, 44, 3885-3889
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3885-3889

34
- 33646348968
- C. Bonaccorsi, F. Santoro, S. Gischig, A. Mezzetti, Organometallics 2006, 25, 2002-2010.
- (2006) Organometallics , vol.25 , pp. 2002-2010
- Bonaccorsi, C.¹ Santoro, F.² Gischig, S.³ Mezzetti, A.⁴

35
- 0142026526
- L. Huang, Y. Chen, G.-Y. Gao, X. P. Zhang, J. Org. Chem. 2003, 68, 8179-8184
- (2003) J. Org. Chem. , vol.68 , pp. 8179-8184
- Huang, L.¹ Chen, Y.² Gao, G.-Y.³ Zhang, X.P.⁴

36
- 8844247934
- Y. Chen, K. B. Fields, X. P. Zhang, J. Am. Chem. Soc. 2004, 126, 14718-14719
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 14718-14719
- Chen, Y.¹ Fields, K.B.² Zhang, X.P.³

37
- 20844436569
- J. Gao, F. R. Woolley, R. A. Zingaro, Org. Biomol. Chem. 2005, 3, 2126-2128
- (2005) Org. Biomol. Chem. , vol.3 , pp. 2126-2128
- Gao, J.¹ Woolley, F.R.² Zingaro, R.A.³

38
- 33744459516
- T. Uchida, T. Katsuki, Synthesis 2006, 1715-1723
- (2006) Synthesis , pp. 1715-1723
- Uchida, T.¹ Katsuki, T.²

39
- 35048898699
- Y. Chen, J. V. Ruppel, X. P. Zhang, J. Am. Chem. Soc. 2007, 129, 12074-12075
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12074-12075
- Chen, Y.¹ Ruppel, J.V.² Zhang, X.P.³

40
- 66149167197
- J. V. Ruppel, T. J. Gauthier, N. L. Snyder, J. A. Perman, X. P. Zhang, Org. Lett. 2009, 11, 2273-2276.
- (2009) Org. Lett. , vol.11 , pp. 2273-2276
- Ruppel, J.V.¹ Gauthier, T.J.² Snyder, N.L.³ Perman, J.A.⁴ Zhang, X.P.⁵

41
- 0037204009
- S. D. Larsen, T. Barf, C. Liljebris, P. D. May, D. Ogg, T. J. O'Sullivan, B. J. Palazuk, H. J. Schostarez, F. C. Stevens, J. E. Bleasdale, J. Med. Chem. 2002, 45, 598-622
- (2002) J. Med. Chem. , vol.45 , pp. 598-622
- Larsen, S.D.¹ Barf, T.² Liljebris, C.³ May, P.D.⁴ Ogg, D.⁵ O'Sullivan, T.J.⁶ Palazuk, B.J.⁷ Schostarez, H.J.⁸ Stevens, F.C.⁹ Bleasdale, J.E.¹⁰

42
- 0012566571
- B. M. Trost, O. Dirat, J. L. Gunzner, Angew. Chem. 2002, 114, 869-871
- (2002) Angew. Chem. , vol.114 , pp. 869-871
- Trost, B.M.¹ Dirat, O.² Gunzner, J.L.³

43
- 0036495731
- Angew. Chem. Int. Ed. 2002, 41, 841-843
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 841-843

44
- 0037019541
- B. M. Trost, J. L. Gunzner, O. Dirat, Y. H. Rhee, J. Am. Chem. Soc. 2002, 124, 10396-10415
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 10396-10415
- Trost, B.M.¹ Gunzner, J.L.² Dirat, O.³ Rhee, Y.H.⁴

45
- 0141827510
- M.-X. Zhang, P. E. Eaton, Angew. Chem. 2002, 114, 2273-2275
- (2002) Angew. Chem. , vol.114 , pp. 2273-2275
- Zhang, M.-X.¹ Eaton, P.E.²

46
- 0037124691
- Angew. Chem. Int. Ed. 2002, 41, 2169-2171
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2169-2171

47
- 0141431047
- J. A. Miller, E. J. Hennessy, W. J. Marshall, M. A. Scialdone, S. T. Nguyen, J. Org. Chem. 2003, 68, 7884-7886
- (2003) J. Org. Chem. , vol.68 , pp. 7884-7886
- Miller, J.A.¹ Hennessy, E.J.² Marshall, W.J.³ Scialdone, M.A.⁴ Nguyen, S.T.⁵

48
- 0037449352
- U. S. Sørensen, T. J. Bleisch, A. E. Kingston, R. A. Wright, B. G. Johnson, D. D. Schoepp, P. L. Ornstein, Bioorg. Med. Chem. 2003, 11, 197-205
- (2003) Bioorg. Med. Chem. , vol.11 , pp. 197-205
- Sørensen, U.S.¹ Bleisch, T.J.² Kingston, A.E.³ Wright, R.A.⁴ Johnson, B.G.⁵ Schoepp, D.D.⁶ Ornstein, P.L.⁷

49
- 12344338114
- J. K. Pokorski, M. C. Myers, D. H. Appella, Tetrahedron Lett. 2005, 46, 915-917
- (2005) Tetrahedron Lett. , vol.46 , pp. 915-917
- Pokorski, J.K.¹ Myers, M.C.² Appella, D.H.³

50
- 69949174806
- K. Kagayama, T. Morimoto, S. Nagata, F. Katoh, X. Zhang, N. Inoue, A. Hashino, K. Kageyama, J. Shikaura, T. Niwa, Bioorg. Med. Chem. 2009, 17, 6959-6970.
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 6959-6970
- Kagayama, K.¹ Morimoto, T.² Nagata, S.³ Katoh, F.⁴ Zhang, X.⁵ Inoue, N.⁶ Hashino, A.⁷ Kageyama, K.⁸ Shikaura, J.⁹ Niwa, T.¹⁰

51
- 82955242164
- A.-M. Abu-Elfotoh, K. Phomkeona, K. Shibatomi, S. Iwasa, Angew. Chem. 2010, 122, 8617-8621
- (2010) Angew. Chem. , vol.122 , pp. 8617-8621
- Abu-Elfotoh, A.-M.¹ Phomkeona, K.² Shibatomi, K.³ Iwasa, S.⁴

52
- 78149446333
- Angew. Chem. Int. Ed. 2010, 49, 8439-8443
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8439-8443

53
- 84863955511
- S. Chanthamath, K. Phomkeona, K. Shibatomi, S. Iwasa, Chem. Commun. 2012, 48, 7750-7752
- (2012) Chem. Commun. , vol.48 , pp. 7750-7752
- Chanthamath, S.¹ Phomkeona, K.² Shibatomi, K.³ Iwasa, S.⁴

54
- 84873962742
- S. Chanthamath, D. T. Nguyen, K. Shibatomi, S. Iwasa, Org. Lett. 2013, 15, 772-775.
- (2013) Org. Lett. , vol.15 , pp. 772-775
- Chanthamath, S.¹ Nguyen, D.T.² Shibatomi, K.³ Iwasa, S.⁴

55
- 0027477118
- K. Hori, H. Kazuno, K. Nomura, E. Yoshii, Tetrahedron Lett. 1993, 34, 2183-2186.
- (1993) Tetrahedron Lett. , vol.34 , pp. 2183-2186
- Hori, K.¹ Kazuno, H.² Nomura, K.³ Yoshii, E.⁴

56
- 79960404839
- T. Goto, K. Takeda, M. Anada, K. Ando, S. Hashimoto, Tetrahedron Lett. 2011, 52, 4200-4203.
- (2011) Tetrahedron Lett. , vol.52 , pp. 4200-4203
- Goto, T.¹ Takeda, K.² Anada, M.³ Ando, K.⁴ Hashimoto, S.⁵

57
- 0029855416
- A. B. Charette, H. Lebel, J. Am. Chem. Soc. 1996, 118, 10327-10328; for the determination of the absolute configuration of 1,2-cyclopropane dimethanol, see
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 10327-10328
- Charette, A.B.¹ Lebel, H.²

58
- 0030923447
- A. G. M. Barrett, D. Hamprecht, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 8608-8615
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 8608-8615
- Barrett, A.G.M.¹ Hamprecht, D.² White, A.J.P.³ Williams, D.J.⁴

59
- 0030932220
- W. S. McDonald, C. A. Verbicky, C. K. Zercher, J. Org. Chem. 1997, 62, 1215-1222.
- (1997) J. Org. Chem. , vol.62 , pp. 1215-1222
- McDonald, W.S.¹ Verbicky, C.A.² Zercher, C.K.³

60
- 0027981564
- For the determination of the absolute configuration of 1,2-cyclopropane dicarboxylic acid, see:, M. P. Singh, B. Plouvier, G. C. Hill, J. Gueck, R. T. Pon, J. W. Lown, J. Am. Chem. Soc. 1994, 116, 7006-7020.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7006-7020
- Singh, M.P.¹ Plouvier, B.² Hill, G.C.³ Gueck, J.⁴ Pon, R.T.⁵ Lown, J.W.⁶

61
- 33644807569
- T. Jiang, K. L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Y.-H. Wu, Y. He, Bioorg. Med. Chem. Lett. 2006, 16, 2105-2108.
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 2105-2108
- Jiang, T.¹ Kuhen, K.L.² Wolff, K.³ Yin, H.⁴ Bieza, K.⁵ Caldwell, J.⁶ Bursulaya, B.⁷ Wu, T.Y.-H.⁸ He, Y.⁹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.