SCOPUS 정보 검색 플랫폼

Chemistry - An Asian Journal

Volumn 6, Issue 10, 2011, Pages 2720-2724

Mitsunobu reaction of 1,2,3-NH-triazoles: A regio- and stereoselective approach to functionalized triazole derivatives

(6) Yan, Wuming a Liao, Tao a Tuguldur, Odbadrakh a Zhong, Cheng a Petersen, Jeffrey L a Shi, Xiaodong a

a WEST VIRGINIA UNIVERSITY (United States)

Author keywords

1,2,3 triazoles; click chemistry; enantioselectivity; Mitsunobu reaction; regioselectivity

Indexed keywords

1 ,2 ,3-TRIAZOLES; CLICK CHEMISTRY; FUNCTIONALIZED; MITSUNOBU REACTIONS; STEREO-SELECTIVE; TRIAZOLE DERIVATIVES;

ENANTIOSELECTIVITY; NITROGEN COMPOUNDS; REGIOSELECTIVITY; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIAZOLES;

EID: 80053461980 PISSN: 18614728 EISSN: 1861471X Source Type: Journal
DOI: 10.1002/asia.201100357 Document Type: Article

Times cited : (44)

References (63)

1
- 0000749443
- H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
- (2001) Angew. Chem. , vol.113 , pp. 2056-2075
- Kolb, H.C.¹ Finn, M.G.² Sharpless, K.B.³

2
- 0000096835
- Angew. Chem. Int. Ed. 2001, 40, 2004-2021
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004-2021

3
- 77949796395
- J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1302-1315.
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1302-1315
- Hein, J.E.¹ Fokin, V.V.²

4
- 79951600096
- T. Nakamura, T. Terashima, K. Ogata, S. Fukuzawa, Org. Lett. 2011, 13, 620-623
- (2011) Org. Lett. , vol.13 , pp. 620-623
- Nakamura, T.¹ Terashima, T.² Ogata, K.³ Fukuzawa, S.⁴

5
- 78249286326
- C. Spiteri, J. E. Moses, Angew. Chem. 2010, 122, 33-36
- (2010) Angew. Chem. , vol.122 , pp. 33-36
- Spiteri, C.¹ Moses, J.E.²

6
- 78249282397
- Angew. Chem. Int. Ed. 2010, 49, 31-33
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 31-33

7
- 77949799806
- C. O. Kappe, E. VanderEycken, Chem. Soc. Rev. 2010, 39, 1280-1290
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1280-1290
- Kappe, C.O.¹ Vandereycken, E.²

8
- 70349144073
- F. Amblard, J. H. Cho, R. F. Schinazi, Chem. Rev. 2009, 109, 4207-4220
- (2009) Chem. Rev. , vol.109 , pp. 4207-4220
- Amblard, F.¹ Cho, J.H.² Schinazi, R.F.³

9
- 48849105709
- F. Shi, J. P. Waldo, Y. Chen, R. C. Larock, Org. Lett. 2008, 10, 2409-2412
- (2008) Org. Lett. , vol.10 , pp. 2409-2412
- Shi, F.¹ Waldo, J.P.² Chen, Y.³ Larock, R.C.⁴

10
- 34547272503
- J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249-1262.
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1249-1262
- Moses, J.E.¹ Moorhouse, A.D.²

11
- 79951540450
- H. Vedala, Y. A. Chen, S. Cecioni, A. Imberty, S. Vidal, A. Star, Nano Lett. 2011, 11, 170-175
- (2011) Nano Lett. , vol.11 , pp. 170-175
- Vedala, H.¹ Chen, Y.A.² Cecioni, S.³ Imberty, A.⁴ Vidal, S.⁵ Star, A.⁶

12
- 77949812304
- P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338-1354
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1338-1354
- Golas, P.L.¹ Matyjaszewski, K.²

13
- 67949112461
- K. Matyjaszewski, N. V. Tsarevsky, Nat. Chem. 2009, 1, 276-288
- (2009) Nat. Chem. , vol.1 , pp. 276-288
- Matyjaszewski, K.¹ Tsarevsky, N.V.²

14
- 42149164860
- K. L. Killops, L. M. Campos, C. J. Hawker, J. Am. Chem. Soc. 2008, 130, 5062-5064
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 5062-5064
- Killops, K.L.¹ Campos, L.M.² Hawker, C.J.³

15
- 34547482973
- D. Fournier, R. Hoogenboom, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1369-1380
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1369-1380
- Fournier, D.¹ Hoogenboom, R.² Schubert, U.S.³

16
- 33846703461
- W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2007, 28, 15-54.
- (2007) Macromol. Rapid Commun. , vol.28 , pp. 15-54
- Binder, W.H.¹ Sachsenhofer, R.²

17
- 79952169959
- J. Schulz, D. Vimont, T. Bordenave, D. James, J. M. Escudier, M. Allard, M. Szlosek-Pinaud, E. Fouquet, Chem. Eur. J. 2011, 17, 3096-3100
- (2011) Chem. Eur. J. , vol.17 , pp. 3096-3100
- Schulz, J.¹ Vimont, D.² Bordenave, T.³ James, D.⁴ Escudier, J.M.⁵ Allard, M.⁶ Szlosek-Pinaud, M.⁷ Fouquet, E.⁸

18
- 77949863611
- J. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272-1279
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1272-1279
- Jewett, J.C.¹ Bertozzi, C.R.²

19
- 77949779995
- A. H. El-Sagheer, T. Brown, Chem. Soc. Rev. 2010, 39, 1388-1405
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1388-1405
- El-Sagheer, A.H.¹ Brown, T.²

20
- 70349084150
- L. S. Wong, F. Khan, J. Micklefield, Chem. Rev. 2009, 109, 4025-4053
- (2009) Chem. Rev. , vol.109 , pp. 4025-4053
- Wong, L.S.¹ Khan, F.² Micklefield, J.³

21
- 60849097580
- G. J. Chen, S. Amajjahe, M. H. Stenzel, Chem. Commun. 2009, 1198-1200
- (2009) Chem. Commun. , pp. 1198-1200
- Chen, G.J.¹ Amajjahe, S.² Stenzel, M.H.³

22
- 43449108552
- J. F. Lutz, Z. Zarafshani, Adv. Drug Delivery Rev. 2008, 60, 958-970
- (2008) Adv. Drug Delivery Rev. , vol.60 , pp. 958-970
- Lutz, J.F.¹ Zarafshani, Z.²

23
- 33846692923
- L. J. Macpherson, A. E. Dubin, M. J. Evans, F. Marr, P. G. Schultz, B. F. Cravatt, A. Patapoutian, Nature 2007, 445, 541-545.
- (2007) Nature , vol.445 , pp. 541-545
- MacPherson, L.J.¹ Dubin, A.E.² Evans, M.J.³ Marr, F.⁴ Schultz, P.G.⁵ Cravatt, B.F.⁶ Patapoutian, A.⁷

24
- 77949857925
- M. G. Finn, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1231-1232.
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1231-1232
- Finn, M.G.¹ Fokin, V.V.²

25
- 77951784445
- L. Ackermann, R. Jeyachandran, H. K. Potukuchi, P. Novak, L. Buttner, Org. Lett. 2010, 12, 2056-2059
- (2010) Org. Lett. , vol.12 , pp. 2056-2059
- Ackermann, L.¹ Jeyachandran, R.² Potukuchi, H.K.³ Novak, P.⁴ Buttner, L.⁵

26
- 77149145205
- H. F. Jiang, Z. N. Feng, A. Z. Wang, X. H. Liu, Z. W. Chen, Eur. J. Org. Chem. 2010, 1227-1230
- (2010) Eur. J. Org. Chem. , pp. 1227-1230
- Jiang, H.F.¹ Feng, Z.N.² Wang, A.Z.³ Liu, X.H.⁴ Chen, Z.W.⁵

27
- 53849088886
- L. Ackermann, R. Vicente, R. Born, Adv. Synth. Catal. 2008, 350, 741-748
- (2008) Adv. Synth. Catal. , vol.350 , pp. 741-748
- Ackermann, L.¹ Vicente, R.² Born, R.³

28
- 34250864418
- S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett. 2007, 9, 2333-2336.
- (2007) Org. Lett. , vol.9 , pp. 2333-2336
- Chuprakov, S.¹ Chernyak, N.² Dudnik, A.S.³ Gevorgyan, V.⁴

29
- 78649879356
- K. J. Kilpin, U. S. D. Paul, A. L. Lee, J. D. Crowley, Chem. Commun. 2011, 47, 328-330
- (2011) Chem. Commun. , vol.47 , pp. 328-330
- Kilpin, K.J.¹ Paul, U.S.D.² Lee, A.L.³ Crowley, J.D.⁴

30
- 79551702027
- K. Ohmatsu, M. Kiyokawa, T. Ooi, J. Am. Chem. Soc. 2011, 133, 1307-1309
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 1307-1309
- Ohmatsu, K.¹ Kiyokawa, M.² Ooi, T.³

31
- 78449236419
- G. Guisado-Barrios, J. Bouffard, B. Donnadieu, G. Bertrand, Angew. Chem. 2010, 122, 4869-4872
- (2010) Angew. Chem. , vol.122 , pp. 4869-4872
- Guisado-Barrios, G.¹ Bouffard, J.² Donnadieu, B.³ Bertrand, G.⁴

32
- 77954027024
- Angew. Chem. Int. Ed. 2010, 49, 4759-4762
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4759-4762

33
- 53849083121
- P. Mathew, A. Neels, M. Albrecht, J. Am. Chem. Soc. 2008, 130, 13534-13535
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 13534-13535
- Mathew, P.¹ Neels, A.² Albrecht, M.³

34
- 47349098606
- B. C. Boren, S. Narayan, L. K. Rasmussen, L. Zhang, H. T. Zhao, Z. Y. Lin, G. C. Jia, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 8923-8930
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8923-8930
- Boren, B.C.¹ Narayan, S.² Rasmussen, L.K.³ Zhang, L.⁴ Zhao, H.T.⁵ Lin, Z.Y.⁶ Jia, G.C.⁷ Fokin, V.V.⁸

35
- 72449165436
- S. Chuprakov, S. W. Kwok, L. Zhang, L. Lercher, V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034-18305
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 18034-18305
- Chuprakov, S.¹ Kwok, S.W.² Zhang, L.³ Lercher, L.⁴ Fokin, V.V.⁵

36
- 77950337980
- N. Grimster, L. Zhang, V. V. Fokin, J. Am. Chem. Soc. 2010, 132, 2510-2511.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2510-2511
- Grimster, N.¹ Zhang, L.² Fokin, V.V.³

37
- 77953584610
- B. Schulze, C. Friebe, M. D. Hager, W. Gunther, U. Kohn, B. O. Jahn, H. Gorls, U. S. Schubert, Org. Lett. 2010, 12, 2710-2713
- (2010) Org. Lett. , vol.12 , pp. 2710-2713
- Schulze, B.¹ Friebe, C.² Hager, M.D.³ Gunther, W.⁴ Kohn, U.⁵ Jahn, B.O.⁶ Gorls, H.⁷ Schubert, U.S.⁸

38
- 77953482004
- B. Happ, D. Escudero, M. D. Hager, C. Friebe, A. Winter, H. Gorls, E. Altuntas, L. Gonzalez, U. S. Schubert, J. Org. Chem. 2010, 75, 4025-4038
- (2010) J. Org. Chem. , vol.75 , pp. 4025-4038
- Happ, B.¹ Escudero, D.² Hager, M.D.³ Friebe, C.⁴ Winter, A.⁵ Gorls, H.⁶ Altuntas, E.⁷ Gonzalez, L.⁸ Schubert, U.S.⁹

39
- 78049369511
- O. Fleischel, N. Wu, A. Petitjean, Chem. Commun. 2010, 46, 8454-8456
- (2010) Chem. Commun. , vol.46 , pp. 8454-8456
- Fleischel, O.¹ Wu, N.² Petitjean, A.³

40
- 73349135907
- M. Felici, P. Contreras-Carballada, Y. Vida, J. M. M. Smits, R. J. M. Nolte, L. DeCola, R. M. Williams, M. C. Feiters, Chem. Eur. J. 2009, 15, 13124-13134
- (2009) Chem. Eur. J. , vol.15 , pp. 13124-13134
- Felici, M.¹ Contreras-Carballada, P.² Vida, Y.³ Smits, J.M.M.⁴ Nolte, R.J.M.⁵ Decola, L.⁶ Williams, R.M.⁷ Feiters, M.C.⁸

41
- 34347253034
- Y. J. Li, J. C. Huffman, A. H. Flood, Chem. Commun. 2007, 2692-2694.
- (2007) Chem. Commun. , pp. 2692-2694
- Li, Y.J.¹ Huffman, J.C.² Flood, A.H.³

42
- 61349179599
- S. W. Kwok, J. E. Hein, V. V. Fokin, K. B. Sharpless, Heterocycles 2008, 76, 1141-1154
- (2008) Heterocycles , vol.76 , pp. 1141-1154
- Kwok, S.W.¹ Hein, J.E.² Fokin, V.V.³ Sharpless, K.B.⁴

43
- 72449173361
- X. J. Wang, K. Sidhu, L. Zhang, S. Campbell, N. Haddad, D. C. Reeves, D. Krishnamurthy, C. H. Senanayake, Org. Lett. 2009, 11, 5490-5493
- (2009) Org. Lett. , vol.11 , pp. 5490-5493
- Wang, X.J.¹ Sidhu, K.² Zhang, L.³ Campbell, S.⁴ Haddad, N.⁵ Reeves, D.C.⁶ Krishnamurthy, D.⁷ Senanayake, C.H.⁸

44
- 77957847870
- X. J. Wang, L. Zhang, D. Krishnamurthy, C. H. Senanayake, P. Wipf, Org. Lett. 2010, 12, 4632-4635
- (2010) Org. Lett. , vol.12 , pp. 4632-4635
- Wang, X.J.¹ Zhang, L.² Krishnamurthy, D.³ Senanayake, C.H.⁴ Wipf, P.⁵

45
- 70350678977
- X. J. Wang, L. Zhang, H. Lee, N. Haddad, D. Krishnamurthy, C. H. Senanayake, Org. Lett. 2009, 11, 5026-5028.
- (2009) Org. Lett. , vol.11 , pp. 5026-5028
- Wang, X.J.¹ Zhang, L.² Lee, H.³ Haddad, N.⁴ Krishnamurthy, D.⁵ Senanayake, C.H.⁶

46
- 61349086057
- Y. Liu, W. Yan, Y. Chen, J. L. Petersen, X. Shi, Org. Lett. 2008, 10, 5389-5392
- (2008) Org. Lett. , vol.10 , pp. 5389-5392
- Liu, Y.¹ Yan, W.² Chen, Y.³ Petersen, J.L.⁴ Shi, X.⁵

47
- 47249148754
- Y. Chen, Y. Liu, J. L. Petersen, X. Shi, Chem. Commun. 2008, 3254-3256
- (2008) Chem. Commun. , pp. 3254-3256
- Chen, Y.¹ Liu, Y.² Petersen, J.L.³ Shi, X.⁴

48
- 67649641716
- H. Duan, W. Yan, S. Sengupta, X. Shi, Bioorg. Med. Chem. Lett. 2009, 19, 3899-3902
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3899-3902
- Duan, H.¹ Yan, W.² Sengupta, S.³ Shi, X.⁴

49
- 77955128787
- W. Yan, Q. Wang, Y. Chen, J. L. Petersen, X. Shi, Org. Lett. 2010, 12, 3308-3311
- (2010) Org. Lett. , vol.12 , pp. 3308-3311
- Yan, W.¹ Wang, Q.² Chen, Y.³ Petersen, J.L.⁴ Shi, X.⁵

50
- 47249121513
- S. Sengupta, H. F. Duan, W. B. Lu, J. L. Petersen, X. D. Shi, Org. Lett. 2008, 10, 1493-1496.
- (2008) Org. Lett. , vol.10 , pp. 1493-1496
- Sengupta, S.¹ Duan, H.F.² Lu, W.B.³ Petersen, J.L.⁴ Shi, X.D.⁵

51
- 79954618319
- W. Yan, Q. Wang, Q. Lin, M. Li, J. L. Peterse, X. Shi, Chem. Eur. J. 2011, 17, 5011-5018.
- (2011) Chem. Eur. J. , vol.17 , pp. 5011-5018
- Yan, W.¹ Wang, Q.² Lin, Q.³ Li, M.⁴ Peterse, J.L.⁵ Shi, X.⁶

52
- 77955799457
- Y. Chen, D. Wang, J. L. Petersen, N. G. Akhmedov, X. Shi, Chem. Commun. 2010, 46, 6147-6149
- (2010) Chem. Commun. , vol.46 , pp. 6147-6149
- Chen, Y.¹ Wang, D.² Petersen, J.L.³ Akhmedov, N.G.⁴ Shi, X.⁵

53
- 77951779135
- D. Wang, X. Ye, X. Shi, Org. Lett. 2010, 12, 2088-2091
- (2010) Org. Lett. , vol.12 , pp. 2088-2091
- Wang, D.¹ Ye, X.² Shi, X.³

54
- 74949123121
- Y. Chen, W. Yan, N. G. Akhmedov, X. Shi, Org. Lett. 2010, 12, 344-347
- (2010) Org. Lett. , vol.12 , pp. 344-347
- Chen, Y.¹ Yan, W.² Akhmedov, N.G.³ Shi, X.⁴

55
- 69349103442
- H. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc. 2009, 131, 12100-12102
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12100-12102
- Duan, H.¹ Sengupta, S.² Petersen, J.L.³ Akhmedov, N.G.⁴ Shi, X.⁵

56
- 65649111557
- H. Duan, S. Sengupta, J. L. Petersen, X. Shi, Organometallics 2009, 28, 2352-2355
- (2009) Organometallics , vol.28 , pp. 2352-2355
- Duan, H.¹ Sengupta, S.² Petersen, J.L.³ Shi, X.⁴

57
- 70350311138
- W. Liao, Y. Chen, H. Duan, Y. Liu, J. L. Petersen, X. Shi, Chem. Commun. 2009, 6436-6438.
- (2009) Chem. Commun. , pp. 6436-6438
- Liao, W.¹ Chen, Y.² Duan, H.³ Liu, Y.⁴ Petersen, J.L.⁵ Shi, X.⁶

58
- 33645364955
- A. Parenty, X. Moreau, J. M. Campagne, Chem. Rev. 2006, 106, 911-939
- (2006) Chem. Rev. , vol.106 , pp. 911-939
- Parenty, A.¹ Moreau, X.² Campagne, J.M.³

59
- 35948981094
- T. Y. S. But, P. H. Toy, Chem. Asian J. 2007, 2, 1340-1355
- (2007) Chem. Asian J. , vol.2 , pp. 1340-1355
- But, T.Y.S.¹ Toy, P.H.²

60
- 67649386488
- K. C. K. Swamy, N. N. B. Kumar, E. Balaraman, K. Kumar, Chem. Rev. 2009, 109, 2551-2651.
- (2009) Chem. Rev. , vol.109 , pp. 2551-2651
- Swamy, K.C.K.¹ Kumar, N.N.B.² Balaraman, E.³ Kumar, K.⁴

61
- 80053469816
- The relative stereochemistry of 6a - 6d were determined by NMR analysis
- The relative stereochemistry of 6a-6d were determined by NMR analysis.

62
- 80053473593
- 2, c=1.0), which confirmed that the likely similar excellent stereochemistry inversion was associated with the product
- 2, c=1.0), which confirmed that the likely similar excellent stereochemistry inversion was associated with the product.

63
- 80053477248
- CCDC819067 (N2- 7b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via
- CCDC819067 (N2- 7b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.