SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 132, Issue 44, 2010, Pages 15800-15807

Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: Rapid access to biologically active pyrroles and indoles

(3) Trost, Barry M a Osipov, Maksim a Dong, Guangbin a

a STANFORD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ALKYLATION; AZIRIDINES; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS; LONGAMIDE B METHYL ESTER; MEDICINAL CHEMISTRY; NITROGEN HETEROCYCLES; SYNTHETIC UTILITY;

CATALYSIS; ENANTIOSELECTIVITY; ESTERS; LEAD COMPOUNDS;

PALLADIUM;

AGESAMIDE A; AGESAMIDE B; ALKALOID DERIVATIVE; AZIRIDINE DERIVATIVE; CYCLOOROIDIN; FUSED CARBON NITROGEN HETEROCYCLE; HANISHIN; INDOLE DERIVATIVE; LONGAMIDE B; LONGAMIDE B METHYL ESTER; NUCLEOPHILE; PALLADIUM; PIPERAZINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; BIOLOGICAL ACTIVITY; BIOTRANSFORMATION; CHIRALITY; CYCLOADDITION; DRUG STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

AZIRIDINES; CATALYSIS; DRUG DESIGN; HETEROCYCLIC COMPOUNDS; INDOLES; MOLECULAR STRUCTURE; NITROGEN; PALLADIUM; PYRROLES; VINYL COMPOUNDS;

EID: 78149258014 PISSN: 00027863 EISSN: 15205126 Source Type: Journal
DOI: 10.1021/ja1071509 Document Type: Article

Times cited : (207)

References (56)

1
- 6844254916
- Trost, B. M. and Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422
- (1996) Chem. Rev. , vol.96 , pp. 395-422
- Trost, B.M.¹ Van Vranken, D.L.²

2
- 0042379988
- Trost, B. M. and Crawley, M. L. Chem. Rev. 2003, 103, 2921-2944
- (2003) Chem. Rev. , vol.103 , pp. 2921-2944
- Trost, B.M.¹ Crawley, M.L.²

3
- 4344566130
- Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837
- (2004) J. Org. Chem. , vol.69 , pp. 5813-5837
- Trost, B.M.¹

4
- 33750620556
- Trost, B. M., Machacek, M. R., and Aponick, A. Acc. Chem. Res. 2006, 39, 747-760
- (2006) Acc. Chem. Res. , vol.39 , pp. 747-760
- Trost, B.M.¹ MacHacek, M.R.² Aponick, A.³

5
- 35048857286
- Trost, B. M. and Fandrick, D. R. Aldrichim. Acta 2007, 40, 59-72
- (2007) Aldrichim. Acta , vol.40 , pp. 59-72
- Trost, B.M.¹ Fandrick, D.R.²

6
- 0033591944
- Trost, B. M. and Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759-6760
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6759-6760
- Trost, B.M.¹ Schroeder, G.M.²

7
- 33846135054
- Trost, B. M. and Zhang, T. Org. Lett. 2006, 8, 6007-6010
- (2006) Org. Lett. , vol.8 , pp. 6007-6010
- Trost, B.M.¹ Zhang, T.²

8
- 54849431595
- Trost, B. M. and Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092-14093
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14092-14093
- Trost, B.M.¹ Thaisrivongs, D.A.²

9
- 69349099076
- Trost, B. M. and Thaisrivongs, D. A. J. Am. Chem. Soc. 2009, 131, 12056-12057
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12056-12057
- Trost, B.M.¹ Thaisrivongs, D.A.²

10
- 0037071923
- Trost, B. M., Kriche, M. J., and Grenzer, E. M. Org. Lett. 2002, 4, 2005-2008
- (2002) Org. Lett. , vol.4 , pp. 2005-2008
- Trost, B.M.¹ Kriche, M.J.² Grenzer, E.M.³

11
- 33646504646
- Trost, B. M. and Dong, G. J. Am. Chem. Soc. 2006, 128, 6054-6055
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6054-6055
- Trost, B.M.¹ Dong, G.²

12
- 34250824037
- Trost, B. M. and Dong, G. Org. Lett. 2007, 9, 2357-2359
- (2007) Org. Lett. , vol.9 , pp. 2357-2359
- Trost, B.M.¹ Dong, G.²

13
- 0034725412
- Trost, B. M., Bunt, R. C., Lemoine, R. C., and Calkins, T. L. J. Am. Chem. Soc. 2000, 122, 5968-5976
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 5968-5976
- Trost, B.M.¹ Bunt, R.C.² Lemoine, R.C.³ Calkins, T.L.⁴

14
- 14844285470
- Somei, M. and Yamada, F. Nat. Prod. Rep. 2005, 22, 73-103
- (2005) Nat. Prod. Rep. , vol.22 , pp. 73-103
- Somei, M.¹ Yamada, F.²

15
- 77949372205
- Thirumalairajan, S., Pearce, B. M., and Thompson, A. Chem. Commun. 2010, 46, 1797-1812
- (2010) Chem. Commun. , vol.46 , pp. 1797-1812
- Thirumalairajan, S.¹ Pearce, B.M.² Thompson, A.³

16
- 78149268932
- For a review on their total syntheses, see
- For a review on their total syntheses, see

17
- 34848832308
- Weinreb, S. M. Nat. Prod. Rep. 2007, 24, 931-948
- (2007) Nat. Prod. Rep. , vol.24 , pp. 931-948
- Weinreb, S.M.¹

18
- 77957027740
- In;, Ed.; Academic Press.: Orlando,; Vol. 24
- Christophersen, C. In The Alkaloids; Brossi, A., Ed.; Academic Press.: Orlando, 1985; Vol. 24, pp 25 - 98.
- (1985) The Alkaloids , pp. 25-98
- Christophersen, C.¹ Brossi, A.²

19
- 0141641722
- Hao, E., Fromont, J., Jardine, D., and Karuso, P. Molecules 2001, 6, 130-141
- (2001) Molecules , vol.6 , pp. 130-141
- Hao, E.¹ Fromont, J.² Jardine, D.³ Karuso, P.⁴

20
- 0027170397
- D'Ambrosio, M., Guerriero, A., Debitus, C., Ribes, O., Pusset, J., Leroy, S., and Pietra, F. J. Chem. Soc., Chem. Commun. 1993, 1305-1306
- (1993) J. Chem. Soc., Chem. Commun. , pp. 1305-1306
- D'Ambrosio, M.¹ Guerriero, A.² Debitus, C.³ Ribes, O.⁴ Pusset, J.⁵ Leroy, S.⁶ Pietra, F.⁷

21
- 0028116772
- D'Ambrosio, M., Guerriero, A., Chiasera, G., and Pietra, F. Helv. Chim. Acta 1994, 77, 1895-1902
- (1994) Helv. Chim. Acta , vol.77 , pp. 1895-1902
- D'Ambrosio, M.¹ Guerriero, A.² Chiasera, G.³ Pietra, F.⁴

22
- 0029904176
- D'Ambrosio, M., Guerriero, A., Ripamonti, M., Debitus, C., Waikedre, J., and Pietra, F. Helv. Chim. Acta 1996, 79, 727-735
- (1996) Helv. Chim. Acta , vol.79 , pp. 727-735
- D'Ambrosio, M.¹ Guerriero, A.² Ripamonti, M.³ Debitus, C.⁴ Waikedre, J.⁵ Pietra, F.⁶

23
- 0034010742
- Maijer, L., Thunnissen, A. M., White, A. W., Garnier, M., Nikolic, M., Tsai, L. H., Walter, J., Cleverley, K. E., Salinas, P. C., Wu, Y. Z., Biernat, J., Mandelkov, E. M., Kim, S. H., and Pettit, G. R. Chem. Biol. 2000, 2, 51-63
- (2000) Chem. Biol. , vol.2 , pp. 51-63
- Maijer, L.¹ Thunnissen, A.M.² White, A.W.³ Garnier, M.⁴ Nikolic, M.⁵ Tsai, L.H.⁶ Walter, J.⁷ Cleverley, K.E.⁸ Salinas, P.C.⁹ Wu, Y.Z.¹⁰ Biernat, J.¹¹ Mandelkov, E.M.¹² Kim, S.H.¹³ Pettit, G.R.¹⁴

24
- 0027212254
- Kinnel, R. B., Gehrken, P.-H., and Scheuer, P. J. J. Am. Chem. Soc. 1993, 115, 3376-3377
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3376-3377
- Kinnel, R.B.¹ Gehrken, P.-H.² Scheuer, P.J.³

25
- 76249090242
- Seiple, I. B., Su, S., Young, I. S., Lewis, C. A., Yamaguchi, J., and Baran, P. S. Angew. Chem., Int. Ed. 2010, 49, 1095-1098
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 1095-1098
- Seiple, I.B.¹ Su, S.² Young, I.S.³ Lewis, C.A.⁴ Yamaguchi, J.⁵ Baran, P.S.⁶

26
- 0030877326
- Mancini, I., Guella, G., Amade, P., Roussakis, C., and Pietra, F. Tetrahedron Lett. 1997, 38, 6271-6274
- (1997) Tetrahedron Lett. , vol.38 , pp. 6271-6274
- Mancini, I.¹ Guella, G.² Amade, P.³ Roussakis, C.⁴ Pietra, F.⁵

27
- 0031730201
- Umeyama, A., Ito, S., Yuasa, E., Arihara, S., and Yamada, T. J. Nat. Prod. 1998, 61, 1433-1434
- (1998) J. Nat. Prod. , vol.61 , pp. 1433-1434
- Umeyama, A.¹ Ito, S.² Yuasa, E.³ Arihara, S.⁴ Yamada, T.⁵

28
- 0033779742
- Srinivasa Reddy, N. and Venkateswarlu, Y. Biochem. Syst. Ecol. 2000, 28, 1035-1037
- (2000) Biochem. Syst. Ecol. , vol.28 , pp. 1035-1037
- Srinivasa Reddy, N.¹ Venkateswarlu, Y.²

29
- 0034627361
- Fattorusso, E. and Taglialatela-Scafati, O. Tetrahedron Lett. 2000, 41, 9917-9922
- (2000) Tetrahedron Lett. , vol.41 , pp. 9917-9922
- Fattorusso, E.¹ Taglialatela-Scafati, O.²

30
- 33749012529
- Tsuda, M., Yasuda, T., Fukushi, E., Kawabata, J., Sekiguchi, M., Fromont, J., and Kobayashi, J. Org. Lett. 2006, 8, 4235-4238
- (2006) Org. Lett. , vol.8 , pp. 4235-4238
- Tsuda, M.¹ Yasuda, T.² Fukushi, E.³ Kawabata, J.⁴ Sekiguchi, M.⁵ Fromont, J.⁶ Kobayashi, J.⁷

31
- 78149262625
- PCT Int. Appl. WO 02/072584 A2
- Hebeisen, P., Mattei, P., Muller, M., Richter, H., Roever, S., and Taylor, S. PCT Int. Appl. WO 02/072584 A2, 2002.
- (2002)
- Hebeisen, P.¹ Mattei, P.² Muller, M.³ Richter, H.⁴ Roever, S.⁵ Taylor, S.⁶

32
- 78149260907
- PCT Int. Appl. WO US 2006/0128712 A1
- Jolidon, S., Narquizian, R., Norcross, R. D., and Pinard, E. PCT Int. Appl. WO US 2006/0128712 A1, 2006.
- (2006)
- Jolidon, S.¹ Narquizian, R.² Norcross, R.D.³ Pinard, E.⁴

33
- 78149270933
- PCT Int. Appl. WO US 2007/0135416 A1
- Nettekoven, M., Plancher, J.-M., Richter, H., Roche, O., and Taylor, S. PCT Int. Appl. WO US 2007/0135416 A1, 2007.
- (2007)
- Nettekoven, M.¹ Plancher, J.-M.² Richter, H.³ Roche, O.⁴ Taylor, S.⁵

34
- 0036018611
- Dinsmore, C. J. and Beshore, D. C. Org. Prep. Proced. 2002, 34, 367-404
- (2002) Org. Prep. Proced. , vol.34 , pp. 367-404
- Dinsmore, C.J.¹ Beshore, D.C.²

35
- 0037138701
- For recent examples, see
- For recent examples, see: Austin, J. F. and Macmillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1172-1173
- Austin, J.F.¹ MacMillan, D.W.C.²

36
- 0042233997
- Evans, D. A., Scheidt, K. A., Fandrick, K. R., Lam, H. W., and Wu, J. J. Am. Chem. Soc. 2003, 125, 10780-10781
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 10780-10781
- Evans, D.A.¹ Scheidt, K.A.² Fandrick, K.R.³ Lam, H.W.⁴ Wu, J.⁵

37
- 33646557360
- Trost, B. M. and Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314-6315
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6314-6315
- Trost, B.M.¹ Quancard, J.²

38
- 39749091670
- Trost, B. M. and Müller, C. J. Am. Chem. Soc. 2008, 130, 2438-2439
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2438-2439
- Trost, B.M.¹ Müller, C.²

39
- 70349783582
- Cui, H.-L., Feng, X., Peng, J., Lei, J., Jiang, K., and Chen, Y.-C. Angew. Chem., Int. Ed. 2009, 48, 5737-5740
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5737-5740
- Cui, H.-L.¹ Feng, X.² Peng, J.³ Lei, J.⁴ Jiang, K.⁵ Chen, Y.-C.⁶

40
- 45549106383
- Bandini, M., Eichholzer, A., Tragni, M., and Umani-Ronchi, A. Angew. Chem., Int. Ed. 2008, 47, 3238-3241
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3238-3241
- Bandini, M.¹ Eichholzer, A.² Tragni, M.³ Umani-Ronchi, A.⁴

41
- 78149271220
- Stanley, L. M. and Hartwig, J. F. Angew. Chem., Int. Ed. 2009, 48, 5737-5740
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5737-5740
- Stanley, L.M.¹ Hartwig, J.F.²

42
- 0026418434
- Trost, B. M. Science 1991, 254, 1471-1477
- (1991) Science , vol.254 , pp. 1471-1477
- Trost, B.M.¹

43
- 33750309194
- Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259-281
- (1995) Angew. Chem., Int. Ed. , vol.34 , pp. 259-281
- Trost, B.M.¹

44
- 0141843601
- Trost, B. M. and Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11836-11837
- Trost, B.M.¹ Fandrick, D.R.²

45
- 34548083986
- Trost, B. M., Fandrick, D. R., Brodmann, T., and Stiles, D. T. Angew. Chem., Int. Ed. 2007, 46, 6123-6125
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 6123-6125
- Trost, B.M.¹ Fandrick, D.R.² Brodmann, T.³ Stiles, D.T.⁴

46
- 78149248101
- For Pd catalysis with vinyl aziridines, see
- For Pd catalysis with vinyl aziridines, see

47
- 0034703341
- Butler, A. C. D., Inman, G. A., and Alper, H. J. Org. Chem. 2000, 65, 5887-5890
- (2000) J. Org. Chem. , vol.65 , pp. 5887-5890
- Butler, A.C.D.¹ Inman, G.A.² Alper, H.³

48
- 2342550559
- Dong, C. and Alper, H. Tetrahedron: Asymmetry 2004, 15, 1537-1540
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 1537-1540
- Dong, C.¹ Alper, H.²

49
- 23044440202
- Sebelius, S., Olsson, V. J., and Szabó, K. J. Am. Chem. Soc. 2005, 127, 10478-10479
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 10478-10479
- Sebelius, S.¹ Olsson, V.J.² Szabó, K.³

50
- 75649116403
- Fontana, F., Tron, G. C., Barbero, N., Ferrini, S., Thomas, S. P., and Aggarwal, V. K. Chem. Commun. 2010, 46, 267-269
- (2010) Chem. Commun. , vol.46 , pp. 267-269
- Fontana, F.¹ Tron, G.C.² Barbero, N.³ Ferrini, S.⁴ Thomas, S.P.⁵ Aggarwal, V.K.⁶

51
- 48849108177
- Kagawa, N., Malerich, J. P., and Rawal, V. H. Org. Lett. 2008, 10, 2381-2384
- (2008) Org. Lett. , vol.10 , pp. 2381-2384
- Kagawa, N.¹ Malerich, J.P.² Rawal, V.H.³

52
- 0032795262
- Banwell, M. G., Bray, A. M., Willis, A. C., and Wong, D. J. New J. Chem. 1999, 23, 687-690
- (1999) New J. Chem. , vol.23 , pp. 687-690
- Banwell, M.G.¹ Bray, A.M.² Willis, A.C.³ Wong, D.J.⁴

53
- 27444436814
- Patel, J., Pelloux-Léon, N., Minassian, F., and Vallée, Y. J. Org. Chem. 2005, 70, 9081-9084
- (2005) J. Org. Chem. , vol.70 , pp. 9081-9084
- Patel, J.¹ Pelloux-Léon, N.² Minassian, F.³ Vallée, Y.⁴

54
- 27744605691
- Papeo, G., Gómez-Zurita Frau, M. A., Borghi, D., and Varasi, M. Tetrahedron Lett. 2005, 46, 8635-8638
- (2005) Tetrahedron Lett. , vol.46 , pp. 8635-8638
- Papeo, G.¹ Gómez-Zurita Frau, M.A.² Borghi, D.³ Varasi, M.⁴

55
- 33745444854
- Patel, J., Pelloux-Léon, N., Minassian, F., and Vallée, Y. Tetrahedron Lett. 2006, 47, 5561-5563
- (2006) Tetrahedron Lett. , vol.47 , pp. 5561-5563
- Patel, J.¹ Pelloux-Léon, N.² Minassian, F.³ Vallée, Y.⁴

56
- 0033583714
- Trost, B. M. and Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4545-4554
- Trost, B.M.¹ Toste, F.D.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.