SCOPUS 정보 검색 플랫폼

Volumn 21, Issue 21, 2015, Pages 7705-7708

Asymmetric copper-catalyzed vinylogous mukaiyama michael addition of cyclic dienol silanes to unsaturated α-keto phosphonates

(5) Steinkamp, Anne Dorothee a Frings, Marcus a Thomé, Isabelle a,b Schiffers, Ingo a Bolm, Carsten a

a RWTH AACHEN UNIVERSITY (Germany)

b SCRIPPS RESEARCH INSTITUTE (United States)

Author keywords

asymmetric catalysis; bisoxazolines; copper; vinylogous Mukaiyama Michael addition; keto phosphonates

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL COMPOUNDS; SILANES; STEREOSELECTIVITY;

ASYMMETRIC CATALYSIS; BIS-OXAZOLINES; COPPER CATALYZED; ELECTROPHILES; MUKAIYAMA MICHAEL; PHOSPHONATES; STEREO-SELECTIVE; STEREOGENIC CENTERS;

COPPER;

EID: 84928946131 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201500861 Document Type: Article

Times cited : (23)

References (66)

1
- 77957690100
- C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295-7306
- (2010) Chem. Commun. , vol.46 , pp. 7295-7306
- Hawner, C.¹ Alexakis, A.²

2
- 34249095816
- J. Christoffers, G. Koripelly, A. Rosiak, M. Rössle, Synthesis 2007, 1279-1300
- (2007) Synthesis , pp. 1279-1300
- Christoffers, J.¹ Koripelly, G.² Rosiak, A.³ Rössle, M.⁴

3
- 0035126119
- N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196.
- (2001) Synthesis , pp. 171-196
- Krause, N.¹ Hoffmann-Röder, A.²

4
- 77649329258
- H. Jiang, M. W. Paixão, D. Monge, K. A. Jørgensen, J. Am. Chem. Soc. 2010, 132, 2775-2783
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2775-2783
- Jiang, H.¹ Paixão, M.W.² Monge, D.³ Jørgensen, K.A.⁴

5
- 34547402618
- S. Samanta, J. Krause, T. Mandal, C.-G. Zhao, Org. Lett. 2007, 9, 2745-2748
- (2007) Org. Lett. , vol.9 , pp. 2745-2748
- Samanta, S.¹ Krause, J.² Mandal, T.³ Zhao, C.-G.⁴

6
- 33846613821
- N. Takenaka, J. P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 742-743
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 742-743
- Takenaka, N.¹ Abell, J.P.² Yamamoto, H.³

7
- 34547859223
- D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 129, 10029-10041
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 10029-10041
- Evans, D.A.¹ Fandrick, K.R.² Song, H.-J.³ Scheidt, K.A.⁴ Xu, R.⁵

8
- 33745056216
- S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442-7443
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 7442-7443
- Samanta, S.¹ Zhao, C.-G.²

9
- 0042233997
- D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. W. Lam, J. Wu, 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

10
- 0037025955
- S. Hanessian, P. Compain, Tetrahedron 2002, 58, 6521-6529
- (2002) Tetrahedron , vol.58 , pp. 6521-6529
- Hanessian, S.¹ Compain, P.²

11
- 0001443088
- D. A. Evans, J. S. Johnson, J. Am. Chem. Soc. 1998, 120, 4895-4896.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4895-4896
- Evans, D.A.¹ Johnson, J.S.²

12
- 84875733356
- G. Hou, J. Yu, C. Yu, G. Wu, Z. Miao, Adv. Synth. Catal. 2013, 355, 589-593
- (2013) Adv. Synth. Catal. , vol.355 , pp. 589-593
- Hou, G.¹ Yu, J.² Yu, C.³ Wu, G.⁴ Miao, Z.⁵

13
- 80052775681
- J. Yu, X. Zhao, Z. Miao, R. Chen, Org. Biomol. Chem. 2011, 9, 6721-6726.
- (2011) Org. Biomol. Chem. , vol.9 , pp. 6721-6726
- Yu, J.¹ Zhao, X.² Miao, Z.³ Chen, R.⁴

14
- 84895065381
- M. Frings, I. Thomé, I. Schiffers, F. Pan, C. Bolm, Chem. Eur. J. 2014, 20, 1691-1700.
- (2014) Chem. Eur. J. , vol.20 , pp. 1691-1700
- Frings, M.¹ Thomé, I.² Schiffers, I.³ Pan, F.⁴ Bolm, C.⁵

15
- 84896135761
- M. Kalesse, M. Cordes, G. Symkenberg, H.-H. Lu, Nat. Prod. Rep. 2014, 31, 563-594.
- (2014) Nat. Prod. Rep. , vol.31 , pp. 563-594
- Kalesse, M.¹ Cordes, M.² Symkenberg, G.³ Lu, H.-H.⁴

16
- 84859930791
- V. Bisai, Synthesis 2012, 44, 1453-1463
- (2012) Synthesis , vol.44 , pp. 1453-1463
- Bisai, V.¹

17
- 79955923795
- G. Casiraghi, L. Battistini, C. Curti, G. Rassu, F. Zanardi, Chem. Rev. 2011, 111, 3076-3154
- (2011) Chem. Rev. , vol.111 , pp. 3076-3154
- Casiraghi, G.¹ Battistini, L.² Curti, C.³ Rassu, G.⁴ Zanardi, F.⁵

18
- 23044486219
- S. E. Denmark, J. R. Heemstra, Jr., G. L. Beutner, Angew. Chem. Int. Ed. 2005, 44, 4682-4698
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4682-4698
- Denmark, S.E.¹ Heemstra, J.R.² Beutner, G.L.³

19
- 33646194216
- Angew. Chem. 2005, 117, 4760-4777
- (2005) Angew. Chem. , vol.117 , pp. 4760-4777

20
- 0033690703
- G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929-1972.
- (2000) Chem. Rev. , vol.100 , pp. 1929-1972
- Casiraghi, G.¹ Zanardi, F.² Appendino, G.³ Rassu, G.⁴

21
- 84928962227
- K. Fu, J. Zheng, L. Lin, X. Liu, X. Feng, Chem. Commun. 2015, 51, 3106-3108
- (2015) Chem. Commun. , vol.51 , pp. 3106-3108
- Fu, K.¹ Zheng, J.² Lin, L.³ Liu, X.⁴ Feng, X.⁵

22
- 35548965235
- L. V. Heumann, G. E. Keck, Org. Lett. 2007, 9, 4275-4278
- (2007) Org. Lett. , vol.9 , pp. 4275-4278
- Heumann, L.V.¹ Keck, G.E.²

23
- 77954767740
- M. Frings, D. Goedert, C. Bolm, Chem. Commun. 2010, 46, 5497-5499
- (2010) Chem. Commun. , vol.46 , pp. 5497-5499
- Frings, M.¹ Goedert, D.² Bolm, C.³

24
- 77956359272
- C. Curti, B. Ranieri, L. Battistini, G. Rassu, V. Zambrano, G. Pelosi, G. Casiraghi, F. Zanardi, Adv. Synth. Catal. 2010, 352, 2011-2022
- (2010) Adv. Synth. Catal. , vol.352 , pp. 2011-2022
- Curti, C.¹ Ranieri, B.² Battistini, L.³ Rassu, G.⁴ Zambrano, V.⁵ Pelosi, G.⁶ Casiraghi, G.⁷ Zanardi, F.⁸

25
- 60749122587
- M. Frings, I. Atodiresei, J. Runsink, G. Raabe, C. Bolm, Chem. Eur. J. 2009, 15, 1566-1569.
- (2009) Chem. Eur. J. , vol.15 , pp. 1566-1569
- Frings, M.¹ Atodiresei, I.² Runsink, J.³ Raabe, G.⁴ Bolm, C.⁵

26
- 84917709235
- Y. Gu, Y. Wang, T.-Y. Yu, Y.-M. Liang, P.-F. Xu, Angew. Chem. Int. Ed. 2014, 53, 14128-14131
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 14128-14131
- Gu, Y.¹ Wang, Y.² Yu, T.-Y.³ Liang, Y.-M.⁴ Xu, P.-F.⁵

27
- 84928962228
- Angew. Chem. 2014, 126, 14352-14355
- (2014) Angew. Chem. , vol.126 , pp. 14352-14355

28
- 84900803961
- C. Schneider, F. Abels, Org. Biomol. Chem. 2014, 12, 3531-3543
- (2014) Org. Biomol. Chem. , vol.12 , pp. 3531-3543
- Schneider, C.¹ Abels, F.²

29
- 84860379068
- M. S. Manna, V. Kumar, S. Mukherjee, Chem. Commun. 2012, 48, 5193-5195
- (2012) Chem. Commun. , vol.48 , pp. 5193-5195
- Manna, M.S.¹ Kumar, V.² Mukherjee, S.³

30
- 79952132240
- Y. Zhang, Y.-L. Shao, H.-S. Xu, W. Wang, J. Org. Chem. 2011, 76, 1472-1474
- (2011) J. Org. Chem. , vol.76 , pp. 1472-1474
- Zhang, Y.¹ Shao, Y.-L.² Xu, H.-S.³ Wang, W.⁴

31
- 77955348260
- H. Huang, F. Yu, Z. Jin, W. Li, W. Wu, X. Liang, J. Ye, Chem. Commun. 2010, 46, 5957-5959.
- (2010) Chem. Commun. , vol.46 , pp. 5957-5959
- Huang, H.¹ Yu, F.² Jin, Z.³ Li, W.⁴ Wu, W.⁵ Liang, X.⁶ Ye, J.⁷

32
- 84881041065
- S. Rout, S. K. Ray, V. K. Singh, Org. Biomol. Chem. 2013, 11, 4537-4545
- (2013) Org. Biomol. Chem. , vol.11 , pp. 4537-4545
- Rout, S.¹ Ray, S.K.² Singh, V.K.³

33
- 84875750888
- J. George, B. V. S. Reddy, Adv. Synth. Catal. 2013, 355, 383-388
- (2013) Adv. Synth. Catal. , vol.355 , pp. 383-388
- George, J.¹ Reddy, B.V.S.²

34
- 84857208523
- E. K. Kemppainen, G. Sahoo, A. Valkonen, P. M. Pihko, Org. Lett. 2012, 14, 1086-1089
- (2012) Org. Lett. , vol.14 , pp. 1086-1089
- Kemppainen, E.K.¹ Sahoo, G.² Valkonen, A.³ Pihko, P.M.⁴

35
- 40949136596
- H. Yang, S. Kim, Synlett 2008, 555-560
- (2008) Synlett , pp. 555-560
- Yang, H.¹ Kim, S.²

36
- 0035905168
- G. Desimoni, G. Faita, S. Filippone, M. Mella, M. G. Zampori, M. Zema, Tetrahedron 2001, 57, 10203-10212.
- (2001) Tetrahedron , vol.57 , pp. 10203-10212
- Desimoni, G.¹ Faita, G.² Filippone, S.³ Mella, M.⁴ Zampori, M.G.⁵ Zema, M.⁶

37
- 84870612681
- V. Gupta, S. Sudhir, T. Mandal, C. Schneider, Angew. Chem. Int. Ed. 2012, 51, 12609-12612
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 12609-12612
- Gupta, V.¹ Sudhir, S.² Mandal, T.³ Schneider, C.⁴

38
- 84917686880
- Angew. Chem. 2012, 124, 12778-12781
- (2012) Angew. Chem. , vol.124 , pp. 12778-12781

39
- 0034817259
- D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 4480-4491
- Evans, D.A.¹ Scheidt, K.A.² Johnston, J.N.³ Willis, M.C.⁴

40
- 0033569855
- S. C. Fields, Tetrahedron 1999, 55, 12237-12273
- (1999) Tetrahedron , vol.55 , pp. 12237-12273
- Fields, S.C.¹

41
- 0033213404
- H. Seto, T. Kuzuyama, Nat. Prod. Rep. 1999, 16, 589-596
- (1999) Nat. Prod. Rep. , vol.16 , pp. 589-596
- Seto, H.¹ Kuzuyama, T.²

42
- 84990551109
- J. S. Thayer, Appl. Organomet. Chem. 1989, 3, 203-209.
- (1989) Appl. Organomet. Chem. , vol.3 , pp. 203-209
- Thayer, J.S.¹

43
- 27644536700
- O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 2005, 16, 3295-3340.
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3295-3340
- Kolodiazhnyi, O.I.¹

44
- 1542690351
- R. Engel, Chem. Rev. 1977, 77, 349-367.
- (1977) Chem. Rev. , vol.77 , pp. 349-367
- Engel, R.¹

45
- 84893158885
- M. Bassetti, A. DAnnibale, Curr. Org. Chem. 2013, 17, 2654-2677
- (2013) Curr. Org. Chem. , vol.17 , pp. 2654-2677
- Bassetti, M.¹ Dannibale, A.²

46
- 84884900333
- G. Nemecek, R. Thomas, H. Goesmann, C. Feldmann, J. Podlech, Eur. J. Org. Chem. 2013, 6420-6432
- (2013) Eur. J. Org. Chem. , pp. 6420-6432
- Nemecek, G.¹ Thomas, R.² Goesmann, H.³ Feldmann, C.⁴ Podlech, J.⁵

47
- 84872367704
- J. Fournier, O. Lozano, C. Menozzi, S. Arseniyadis, J. Cossy, Angew. Chem. Int. Ed. 2013, 52, 1257-1261
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 1257-1261
- Fournier, J.¹ Lozano, O.² Menozzi, C.³ Arseniyadis, S.⁴ Cossy, J.⁵

48
- 84875871442
- Angew. Chem. 2013, 125, 1295-1299
- (2013) Angew. Chem. , vol.125 , pp. 1295-1299

49
- 84871960144
- W. Wang, H. Kim, S.-J. Nam, B. J. Rho, H. Kang, J. Nat. Prod. 2012, 75, 2049-2054
- (2012) J. Nat. Prod. , vol.75 , pp. 2049-2054
- Wang, W.¹ Kim, H.² Nam, S.-J.³ Rho, B.J.⁴ Kang, H.⁵

50
- 84869010278
- C. A. Citron, S. M. Wickel, B. Schulz, S. Draeger, J. S. Dickschat, Eur. J. Org. Chem. 2012, 6636-6646
- (2012) Eur. J. Org. Chem. , pp. 6636-6646
- Citron, C.A.¹ Wickel, S.M.² Schulz, B.³ Draeger, S.⁴ Dickschat, J.S.⁵

51
- 84868457671
- R. S. Ferrarini, A. A. Dos Santos, J. V. Comasseto, Tetrahedron 2012, 68, 10601-10610
- (2012) Tetrahedron , vol.68 , pp. 10601-10610
- Ferrarini, R.S.¹ Dos Santos, A.A.² Comasseto, J.V.³

52
- 20444404268
- M. Seitz, O. Reiser, Curr. Opin. Chem. Biol. 2005, 9, 285-292.
- (2005) Curr. Opin. Chem. Biol. , vol.9 , pp. 285-292
- Seitz, M.¹ Reiser, O.²

53
- 84887440622
- S. L. Khokra, J. Monga, A. Husain, M. Vij, R. Saini, Med. Chem. Res. 2013, 22, 5536-5544
- (2013) Med. Chem. Res. , vol.22 , pp. 5536-5544
- Khokra, S.L.¹ Monga, J.² Husain, A.³ Vij, M.⁴ Saini, R.⁵

54
- 53849103644
- J. Boukouvalas, R. P. Loach, J. Org. Chem. 2008, 73, 8109-8112
- (2008) J. Org. Chem. , vol.73 , pp. 8109-8112
- Boukouvalas, J.¹ Loach, R.P.²

55
- 27744559326
- A. Husain, M. S. Y. Khan, S. M. Hasan, M. M. Alam, Eur. J. Med. Chem. 2005, 40, 1394-1404.
- (2005) Eur. J. Med. Chem. , vol.40 , pp. 1394-1404
- Husain, A.¹ Khan, M.S.Y.² Hasan, S.M.³ Alam, M.M.⁴

56
- 84896494752
- X. Jusseau, L. Chabaud, C. Guillou, Tetrahedron 2014, 70, 2595-2615.
- (2014) Tetrahedron , vol.70 , pp. 2595-2615
- Jusseau, X.¹ Chabaud, L.² Guillou, C.³

57
- 77950843946
- M. Frings, I. Atodiresei, Y. Wang, J. Runsink, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 4577-4587
- (2010) Chem. Eur. J. , vol.16 , pp. 4577-4587
- Frings, M.¹ Atodiresei, I.² Wang, Y.³ Runsink, J.⁴ Raabe, G.⁵ Bolm, C.⁶

58
- 58149186445
- J. Sedelmeier, T. Hammerer, C. Bolm, Org. Lett. 2008, 10, 917-920
- (2008) Org. Lett. , vol.10 , pp. 917-920
- Sedelmeier, J.¹ Hammerer, T.² Bolm, C.³

59
- 33646439546
- P. Rémy, M. Langner, C. Bolm, Org. Lett. 2006, 8, 1209-1211
- (2006) Org. Lett. , vol.8 , pp. 1209-1211
- Rémy, P.¹ Langner, M.² Bolm, C.³

60
- 27344433443
- M. Langner, P. Rémy, C. Bolm, Chem. Eur. J. 2005, 11, 6254-6265
- (2005) Chem. Eur. J. , vol.11 , pp. 6254-6265
- Langner, M.¹ Rémy, P.² Bolm, C.³

61
- 9244221087
- M. Langner, C. Bolm, Angew. Chem. Int. Ed. 2004, 43, 5984-5987
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 5984-5987
- Langner, M.¹ Bolm, C.²

62
- 22544465610
- Angew. Chem. 2004, 116, 6110-6113
- (2004) Angew. Chem. , vol.116 , pp. 6110-6113

63
- 0033541094
- D. A. Evans, T. Rovis, M. C. Kozlowski, J. S. Tedrow, J. Am. Chem. Soc. 1999, 121, 1994-1995
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1994-1995
- Evans, D.A.¹ Rovis, T.² Kozlowski, M.C.³ Tedrow, J.S.⁴

64
- 0002691788
- H. Kitajima, T. Katsuki, Synlett 1997, 568-570.
- (1997) Synlett , pp. 568-570
- Kitajima, H.¹ Katsuki, T.²

65
- 4243166669
- The optical rotation of 5 showed that it was enantiomerically enriched (see the Supporting Information for details). The same product was formed when 3 a was stirred in methanol in the absence of DBU. For a synthesis of the racemic diester 5, see:, H. Schick, S. Schwarz, U. Eberhardt, J. Prakt. Chem. 1977, 319, 213-218.
- (1977) J. Prakt. Chem. , vol.319 , pp. 213-218
- Schick, H.¹ Schwarz, S.² Eberhardt, U.³

66
- 0032499189
- H. Nishikori, K. Ito, T. Katsuki, Tetrahedron: Asymmetry 1998, 9, 1165-1170.
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1165-1170
- Nishikori, H.¹ Ito, K.² Katsuki, T.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.