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Volumn 19, Issue 17, 2013, Pages 5250-5254

Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: Highly diastereoselective synthesis of trans-diamines from cycloalkenes

(3) Zhu, Ming Kui b Chen, Yu Chen b Loh, Teck Peng a,b

a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA (China)

b Nanyang Technological University (Singapore)

Author keywords

alkenes; cyclization; diamination; diastereoselectivity; radicals

Indexed keywords

AZODICARBOXYLATES; DIAMINATION; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE SYNTHESIS; METAL-FREE SYNTHESIS; RADICAL MECHANISM; RADICALS; TRANS-SELECTIVITY;

CYCLIZATION; OLEFINS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

HYDROCARBONS;

ALKENE; AZO COMPOUND; CYCLOALKANE DERIVATIVE; DIAMINE; PHENYLHYDRAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; AZO COMPOUNDS; CYCLOPARAFFINS; DIAMINES; MOLECULAR STRUCTURE; PHENYLHYDRAZINES; STEREOISOMERISM;

EID: 84876214532 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201203832 Document Type: Article

Times cited : (58)

References (64)

1
- 0000341815
- D. Lucet, T. L. Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724
- (1998) Angew. Chem. , vol.110 , pp. 2724
- Lucet, D.¹ Gall, T.L.² Mioskowski, C.³

2
- 72149120954
- Angew. Chem. Int. Ed. 1998, 37, 2580
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2580

3
- 38849161554
- J.-C. Kizirian, Chem. Rev. 2008, 108, 140
- (2008) Chem. Rev. , vol.108 , pp. 140
- Kizirian, J.-C.¹

4
- 33745110538
- S. R. S. S. Kotti, C. Timmons, G. Li, Chem. Biol. Drug Des. 2006, 67, 101
- (2006) Chem. Biol. Drug Des. , vol.67 , pp. 101
- Kotti, S.R.S.S.¹ Timmons, C.² Li, G.³

5
- 28144436808
- K. Muñiz, New J. Chem. 2005, 29, 1371.
- (2005) New J. Chem. , vol.29 , pp. 1371
- Muñiz, K.¹

6
- 27144440348
- J. Streuff, C. H. Hövelmann, M. Nieger, K. Muñiz, J. Am. Chem. Soc. 2005, 127, 14586
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 14586
- Streuff, J.¹ Hövelmann, C.H.² Nieger, M.³ Muñiz, K.⁴

7
- 41449087573
- K. Muñiz, C. H. Hövelmann, J. Streuff, J. Am. Chem. Soc. 2008, 130, 763
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 763
- Muñiz, K.¹ Hövelmann, C.H.² Streuff, J.³

8
- 36749031103
- K. Muñiz, J. Am. Chem. Soc. 2007, 129, 14542
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 14542
- Muñiz, K.¹

9
- 43749124197
- C. H. Hövelmann, J. Streuff, L. Brelot, K. Muñiz, Chem. Commun. 2008, 2334
- (2008) Chem. Commun. , pp. 2334
- Hövelmann, C.H.¹ Streuff, J.² Brelot, L.³ Muñiz, K.⁴

10
- 54849420098
- K. Muñiz, J. Streuff, P. Chávez, C. H. Hövelmann, Chem. Asian J. 2008, 3, 1248
- (2008) Chem. Asian J. , vol.3 , pp. 1248
- Muñiz, K.¹ Streuff, J.² Chávez, P.³ Hövelmann, C.H.⁴

11
- 64349118037
- P. A. Sibbald, F. E. Michael, Org. Lett. 2009, 11, 1147
- (2009) Org. Lett. , vol.11 , pp. 1147
- Sibbald, P.A.¹ Michael, F.E.²

12
- 70350662846
- nickel catalysis
- P. A. Sibbald, C. F. Rosewall, R. D. Swartz, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 15945; nickel catalysis
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 15945
- Sibbald, P.A.¹ Rosewall, C.F.² Swartz, R.D.³ Michael, F.E.⁴

13
- 54249111121
- K. Muñiz, J. Streuff, C. H. Hövelmann, A. Nuñez, Angew. Chem. 2007, 119, 7255
- (2007) Angew. Chem. , vol.119 , pp. 7255
- Muñiz, K.¹ Streuff, J.² Hövelmann, C.H.³ Nuñez, A.⁴

14
- 34848915764
- gold catalysis
- Angew. Chem. Int. Ed. 2007, 46, 7125; gold catalysis
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7125

15
- 70349906941
- copper catalysis
- A. Iglesias, K. Muñiz, Chem. Eur. J. 2009, 15, 10563; copper catalysis
- (2009) Chem. Eur. J. , vol.15 , pp. 10563
- Iglesias, A.¹ Muñiz, K.²

16
- 66149172045
- Y. Wen, B. Zhao, Y. Shi, Org. Lett. 2009, 11, 2365
- (2009) Org. Lett. , vol.11 , pp. 2365
- Wen, Y.¹ Zhao, B.² Shi, Y.³

17
- 45549088414
- B. Zhao, H. Du, Y. Shi, Org. Lett. 2008, 10, 1087
- (2008) Org. Lett. , vol.10 , pp. 1087
- Zhao, B.¹ Du, H.² Shi, Y.³

18
- 36849045727
- B. Zhao, W. Yuan, H. Du, Y. Shi, Org. Lett. 2007, 9, 4943.
- (2007) Org. Lett. , vol.9 , pp. 4943
- Zhao, B.¹ Yuan, W.² Du, H.³ Shi, Y.⁴

19
- 79953041583
- A. Iglesias, E. G. Pérez, K. Muñiz, Angew. Chem. 2010, 122, 8286
- (2010) Angew. Chem. , vol.122 , pp. 8286
- Iglesias, A.¹ Pérez, E.G.² Muñiz, K.³

20
- 78249287816
- Angew. Chem. Int. Ed. 2010, 49, 8109
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8109

21
- 79953046572
- K. Muñiz, J. Kirsch, P. Chávez, Adv. Synth. Catal. 2011, 353, 689
- (2011) Adv. Synth. Catal. , vol.353 , pp. 689
- Muñiz, K.¹ Kirsch, J.² Chávez, P.³

22
- 84863230228
- Y.-F. Wang, X. Zhu, S. Chiba, J. Am. Chem. Soc. 2012, 134, 3679
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 3679
- Wang, Y.-F.¹ Zhu, X.² Chiba, S.³

23
- 84863706879
- C. Martínez, K. Muñiz, Angew. Chem. Int. Ed. 2012, 51, 7031.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 7031
- Martínez, C.¹ Muñiz, K.²

24
- 67949124387
- F. Cardona, A. Goti, Nat. Chem. 2009, 1, 269
- (2009) Nat. Chem. , vol.1 , pp. 269
- Cardona, F.¹ Goti, A.²

25
- 70349897724
- R. M. De. Figueiredo, Angew. Chem. 2009, 121, 1212
- (2009) Angew. Chem. , vol.121 , pp. 1212
- Figueiredo, R.M.De.¹

26
- 60149111070
- Angew. Chem. Int. Ed. 2009, 48, 1190
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1190

27
- 44649122664
- K. Muñiz, C. H. Hövelmann, J. Streuff, E. Campos-Gómez, Pure Appl. Chem. 2008, 80, 1089
- (2008) Pure Appl. Chem. , vol.80 , pp. 1089
- Muñiz, K.¹ Hövelmann, C.H.² Streuff, J.³ Campos-Gómez, E.⁴

28
- 19744362485
- G. L. J. Bar, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2005, 127, 7308
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 7308
- Bar, G.L.J.¹ Lloyd-Jones, G.C.² Booker-Milburn, K.I.³

29
- 33846624362
- H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 762
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 762
- Du, H.¹ Zhao, B.² Shi, Y.³

30
- 34250863844
- H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 7496
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 7496
- Du, H.¹ Yuan, W.² Zhao, B.³ Shi, Y.⁴

31
- 34748841069
- H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 11688
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 11688
- Du, H.¹ Yuan, W.² Zhao, B.³ Shi, Y.⁴

32
- 70349925643
- B. Wang, H. Du, Y. Shi, Angew. Chem. 2008, 120, 8348
- (2008) Angew. Chem. , vol.120 , pp. 8348
- Wang, B.¹ Du, H.² Shi, Y.³

33
- 54249146835
- Angew. Chem. Int. Ed. 2008, 47, 8224
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8224

34
- 46949104564
- H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8590
- Du, H.¹ Zhao, B.² Shi, Y.³

35
- 40949088883
- L. Xu, Y. Shi, J. Org. Chem. 2008, 73, 749
- (2008) J. Org. Chem. , vol.73 , pp. 749
- Xu, L.¹ Shi, Y.²

36
- 77949421694
- B. Zhao, H. Du, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 3523; for related copper catalysis
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 3523
- Zhao, B.¹ Du, H.² Cui, S.³ Shi, Y.⁴

37
- 70350719270
- B. Zhao, H. Du, Y. Shi, J. Org. Chem. 2009, 74, 8392
- (2009) J. Org. Chem. , vol.74 , pp. 8392
- Zhao, B.¹ Du, H.² Shi, Y.³

38
- 34547198807
- W. Yuan, H. Du, B. Zhao, Y. Shi, Org. Lett. 2007, 9, 2589
- (2007) Org. Lett. , vol.9 , pp. 2589
- Yuan, W.¹ Du, H.² Zhao, B.³ Shi, Y.⁴

39
- 55449137856
- H. Du, B. Zhao, W. Yuan, Y. Shi, Org. Lett. 2008, 10, 4231
- (2008) Org. Lett. , vol.10 , pp. 4231
- Du, H.¹ Zhao, B.² Yuan, W.³ Shi, Y.⁴

40
- 77955571408
- B. Zhao, X. Peng, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 11009
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 11009
- Zhao, B.¹ Peng, X.² Cui, S.³ Shi, Y.⁴

41
- 84888638479
- B. Zhao, X. Peng, Y. Zhu, T. A. Ramirez, R. G. Cornwall, Y. Shi, J. Am. Chem. Soc. 2010, 132, 20890.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 20890
- Zhao, B.¹ Peng, X.² Zhu, Y.³ Ramirez, T.A.⁴ Cornwall, R.G.⁵ Shi, Y.⁶

42
- 84872421810
- C. Röben, J. A. Souto, Y. González, A. Lishchynskyi, K. Muñiz, Angew. Chem. 2011, 123, 9650
- (2011) Angew. Chem. , vol.123 , pp. 9650
- Röben, C.¹ Souto, J.A.² González, Y.³ Lishchynskyi, A.⁴ Muñiz, K.⁵

43
- 80053158122
- Angew. Chem. Int. Ed. 2011, 50, 9478
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9478

44
- 8744221400
- R. Chung, E. Yu, C. D. Incarvito, D. J. Austin, Org. Lett. 2004, 6, 3881
- (2004) Org. Lett. , vol.6 , pp. 3881
- Chung, R.¹ Yu, E.² Incarvito, C.D.³ Austin, D.J.⁴

45
- 84860474752
- S. D. Jong, D. G. Nosal, D. J. Wardrop, Tetrahedron 2012, 68, 4067
- (2012) Tetrahedron , vol.68 , pp. 4067
- Jong, S.D.¹ Nosal, D.G.² Wardrop, D.J.³

46
- 84857802458
- U. Farid, T. Wirth, Angew. Chem. Int. Ed. 2012, 51, 3462
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3462
- Farid, U.¹ Wirth, T.²

47
- 84860463449
- J. A. Souto, Y. González, A. Iglesias, D. Zian, A. Lishchynskyi, K. Muñiz, Chem. Asian J. 2012, 7, 1103
- (2012) Chem. Asian J. , vol.7 , pp. 1103
- Souto, J.A.¹ González, Y.² Iglesias, A.³ Zian, D.⁴ Lishchynskyi, A.⁵ Muñiz, K.⁶

48
- 84862190705
- P. Chávez, J. Kirsch, C. H. Hövelmann, J. Streuff, M. Martínez-Belmonte, E. C. Escudero-Adán, E. Martin, K, Muñiz, Chem. Sci. 2012, 3, 2375.
- (2012) Chem. Sci. , vol.3 , pp. 2375
- Chávez, P.¹ Kirsch, J.² Hövelmann, C.H.³ Streuff, J.⁴ Martínez-Belmonte, M.⁵ Escudero-Adán, E.C.⁶ Martin, E.⁷ Muñiz, K.⁸

49
- 77953063098
- M. K. Zhu, J. F. Zhao, T. P. Loh, J. Am. Chem. Soc. 2010, 132, 6284-6285
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6284-6285
- Zhu, M.K.¹ Zhao, J.F.² Loh, T.P.³

50
- 82355160816
- M. K. Zhu, J. F. Zhao, T. P. Loh, Org. Lett. 2011, 13, 6308.
- (2011) Org. Lett. , vol.13 , pp. 6308
- Zhu, M.K.¹ Zhao, J.F.² Loh, T.P.³

51
- 77949632348
- R. Lazny, A. Nodzewska, Chem. Rev. 2010, 110, 1386
- (2010) Chem. Rev. , vol.110 , pp. 1386
- Lazny, R.¹ Nodzewska, A.²

52
- 23944491198
- A. Tanitame, Y. Oyamada, K. Ofuji, H. Terauchi, M. Kawasaki, M. Wachi, J. Yamagishi, Bioorg. Med. Chem. Lett. 2005, 15, 4299-4303
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 4299-4303
- Tanitame, A.¹ Oyamada, Y.² Ofuji, K.³ Terauchi, H.⁴ Kawasaki, M.⁵ Wachi, M.⁶ Yamagishi, J.⁷

53
- 3042552189
- A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, J. Yamagishi, J. Med. Chem. 2004, 47, 3693.
- (2004) J. Med. Chem. , vol.47 , pp. 3693
- Tanitame, A.¹ Oyamada, Y.² Ofuji, K.³ Fujimoto, M.⁴ Iwai, N.⁵ Hiyama, Y.⁶ Suzuki, K.⁷ Ito, H.⁸ Terauchi, H.⁹ Kawasaki, M.¹⁰ Nagai, K.¹¹ Wachi, M.¹² Yamagishi, J.¹³

54
- 84876259657
- These data can be obtained free of charge from The Cambridge Crystallographic Data Centre
- CCDC-883322 (3 t), -883323 (3 w), and -888659 (3 b′) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
- CCDC-883322 (3 t), -883323 (3 w), and -888659 (3 b′) Contain the Supplementary Crystallographic Data for this Paper

55
- 78449241104
- V. A. Schmidt, E. J. Alexanian, Angew. Chem. 2010, 122, 4593
- (2010) Angew. Chem. , vol.122 , pp. 4593
- Schmidt, V.A.¹ Alexanian, E.J.²

56
- 77953652929
- Angew. Chem. Int. Ed. 2010, 49, 4491
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4491

57
- 34548705892
- M. Harej, D. Dolenc, J. Org. Chem. 2007, 72, 7214
- (2007) J. Org. Chem. , vol.72 , pp. 7214
- Harej, M.¹ Dolenc, D.²

58
- 0001293891
- A. C. Kovelesky, H. J. Shine, J. Org. Chem. 1988, 53, 1973.
- (1988) J. Org. Chem. , vol.53 , pp. 1973
- Kovelesky, A.C.¹ Shine, H.J.²

59
- 84865437035
- B. Han, X.-L. Yang, R. Fang, W. Yu, C. Wang, X.-Y. Duan, S. Liu, Angew. Chem. Int. Ed. 2012, 51, 8816.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8816
- Han, B.¹ Yang, X.-L.² Fang, R.³ Yu, W.⁴ Wang, C.⁵ Duan, X.-Y.⁶ Liu, S.⁷

60
- 33748339796
- J. Waser, B. Gaspar, H. Nambu, E. M. Carreira, J. Am. Chem. Soc. 2006, 128, 11693
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 11693
- Waser, J.¹ Gaspar, B.² Nambu, H.³ Carreira, E.M.⁴

61
- 79960853853
- V. A. Schmidt, E. J. Alexanian, J. Am. Chem. Soc. 2011, 133, 11402
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 11402
- Schmidt, V.A.¹ Alexanian, E.J.²

62
- 0041400807
- A. Shah, M. V. George, Tetrahedron 1971, 27, 1291. For example of an azodicarboxylate facilitating nitroxyl radical formation, see
- (1971) Tetrahedron , vol.27 , pp. 1291
- Shah, A.¹ George, M.V.²

63
- 0009128984
- E. Grochowski, T. Boleslawska, J. Jurczak, Synthesis 1977, 718
- (1977) Synthesis , pp. 718
- Grochowski, E.¹ Boleslawska, T.² Jurczak, J.³

64
- 84858674177
- M. Hayashi, M. Shibuya, Y. Iwabuchi, J. Org. Chem. 2012, 77, 3005.
- (2012) J. Org. Chem. , vol.77 , pp. 3005
- Hayashi, M.¹ Shibuya, M.² Iwabuchi, Y.³

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