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Chemistry - A European Journal

Volumn 19, Issue 24, 2013, Pages 7696-7700

A rational approach towards a new ferrocenyl pyrrolidine for stereoselective enamine catalysis

(4) Petruzziello, Diego a Stenta, Marco b Mazzanti, Andrea a Cozzi, Pier Giorgio a

a UNIVERSITY OF BOLOGNA (Italy)

b EPFL (Switzerland)

Author keywords

enamines; ferrocene; nitro Michael reaction; organocatalysis; pyrrolidine

Indexed keywords

ENAMINES; FERROCENES; NITRO-MICHAEL REACTION; ORGANOCATALYSIS; PYRROLIDINES;

ADDITION REACTIONS; CATALYSTS; ORGANOMETALLICS; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

AMINE; DRUG DERIVATIVE; FERROUS ION; PROLINE; PYRROLIDINE DERIVATIVE;

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

AMINES; CATALYSIS; FERROUS COMPOUNDS; MOLECULAR STRUCTURE; PROLINE; PYRROLIDINES; STEREOISOMERISM;

EID: 84878539356 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201300959 Document Type: Article

Times cited : (23)

References (72)

1
- 55249111616
- P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232-6265
- (2008) Angew. Chem. , vol.120 , pp. 6232-6265
- Melchiorre, P.¹ Marigo, M.² Carlone, A.³ Bartoli, G.⁴

2
- 53549121402
- Angew. Chem. Int. Ed. 2008, 47, 6138-6171
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6138-6171

3
- 53349170687
- C. F. Barbas III, Angew. Chem. 2008, 120, 44-50
- (2008) Angew. Chem. , vol.120 , pp. 44-50
- Barbas Iii, C.F.¹

4
- 53349123537
- Angew. Chem. Int. Ed. 2008, 47, 42-47
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 42-47

5
- 33745715054
- G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87.
- (2006) Aldrichimica Acta , vol.39 , pp. 79-87
- Lelais, G.¹ MacMillan, D.W.C.²

6
- 70349753180
- S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606-13607
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 13606-13607
- Jones, S.B.¹ Simmons, B.² MacMillan, D.W.C.³

7
- 77957202426
- J. Carpenter, A. B. Northrup, D. M. Chung, J. J. M. Wieners, S.-G. Kim, D. W. C. MacMillan, Angew. Chem. 2008, 120, 3624-3628
- (2008) Angew. Chem. , vol.120 , pp. 3624-3628
- Carpenter, J.¹ Northrup, A.B.² Chung, D.M.³ Wieners, J.J.M.⁴ Kim, S.-G.⁵ MacMillan, D.W.C.⁶

8
- 44049104472
- Angew. Chem. Int. Ed. 2008, 47, 3568-3572.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3568-3572

9
- 68849107137
- J. E. Wilson, A. D. Casarez, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 11332-11333.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 11332-11333
- Wilson, J.E.¹ Casarez, A.D.² MacMillan, D.W.C.³

10
- 52149113820
- D. W. C. MacMillan, Nature 2008, 455, 304-308.
- (2008) Nature , vol.455 , pp. 304-308
- MacMillan, D.W.C.¹

11
- 38349178582
- A. Errkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416-5470.
- (2007) Chem. Rev. , vol.107 , pp. 5416-5470
- Errkilä, A.¹ Majander, I.² Pihko, P.M.³

12
- 38349100690
- S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
- (2007) Chem. Rev. , vol.107 , pp. 5471-5569
- Mukherjee, S.¹ Yang, J.W.² Hoffmann, S.³ List, B.⁴

13
- 84866281848
- H. Mayr, S. Lakhdar, B. Maji, A. R. Ofial, Beilstein J. Org. Chem. 2012, 8, 1458-1478.
- (2012) Beilstein J. Org. Chem. , vol.8 , pp. 1458-1478
- Mayr, H.¹ Lakhdar, S.² Maji, B.³ Ofial, A.R.⁴

14
- 57149117689
- D. Seebach, U. GrosÄlj, D. M. Badine, W. B. Schweizer, A. K. Beck, Helv. Chim. Acta 2008, 91, 1999-2034.
- (2008) Helv. Chim. Acta , vol.91 , pp. 1999-2034
- Seebach, D.¹ Grosälj, U.² Badine, D.M.³ Schweizer, W.B.⁴ Beck, A.K.⁵

15
- 20444486476
- M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807
- (2005) Angew. Chem. , vol.117 , pp. 804-807
- Marigo, M.¹ Wabnitz, T.C.² Fielenbach, D.³ Jørgensen, K.A.⁴

16
- 13444267885
- Angew. Chem. Int. Ed. 2005, 44, 794-797
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 794-797

17
- 33645951837
- Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287
- (2005) Angew. Chem. , vol.117 , pp. 4284-4287
- Hayashi, Y.¹ Gotoh, H.² Hayashi, T.³ Shoji, M.⁴

18
- 22144459070
- Angew. Chem. Int. Ed. 2005, 44, 4212-4215. For reviews see
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4212-4215

19
- 34250669449
- C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042-8046
- (2006) Angew. Chem. , vol.118 , pp. 8042-8046
- Palomo, C.¹ Mielgo, A.²

20
- 33845505476
- Angew. Chem. Int. Ed. 2006, 45, 7876-7880
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7876-7880

21
- 84858633852
- K. L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248-264.
- (2012) Acc. Chem. Res. , vol.45 , pp. 248-264
- Jensen, K.L.¹ Dickmeiss, G.² Jiang, H.³ Albrecht, Ł.⁴ Jørgensen, K.A.⁵

22
- 53249118902
- C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, A. Puente, S. Vera, Angew. Chem. 2007, 119, 8583-8587
- (2007) Angew. Chem. , vol.119 , pp. 8583-8587
- Palomo, C.¹ Landa, A.² Mielgo, A.³ Oiarbide, M.⁴ Puente, A.⁵ Vera, S.⁶

23
- 36148957495
- Angew. Chem. Int. Ed. 2007, 46, 8431-8435.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8431-8435

24
- 67749114507
- T. Kano, H. Mii, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 3450-3451.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3450-3451
- Kano, T.¹ Mii, H.² Maruoka, K.³

25
- 78249284338
- R. Husmann, M. Jçrres, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 12549-12558
- (2010) Chem. Eur. J. , vol.16 , pp. 12549-12558
- Husmann, R.¹ Jçrres, M.² Raabe, G.³ Bolm, C.⁴

26
- 78249271709
- J. O. Bauer, J. Stiller, E. Marquéz Lõpez, K. Strohfeldt, M. Christman, C. Strohmann, Chem. Eur. J. 2010, 16, 12553-12558
- (2010) Chem. Eur. J. , vol.16 , pp. 12553-12558
- Bauer, J.O.¹ Stiller, J.² Marquéz Lõpez, E.³ Strohfeldt, K.⁴ Christman, M.⁵ Strohmann, C.⁶

27
- 80052159472
- K. I. Jentzsch, T. Min, J. I. Etcheson, J. C. Fettinger, A. K. Franz, J. Org. Chem. 2011, 76, 7065-7075.
- (2011) J. Org. Chem. , vol.76 , pp. 7065-7075
- Jentzsch, K.I.¹ Min, T.² Etcheson, J.I.³ Fettinger, J.C.⁴ Franz, A.K.⁵

28
- 0001552544
- R. Noyori, Angew. Chem. 2002, 114, 2108-2123
- (2002) Angew. Chem. , vol.114 , pp. 2108-2123
- Noyori, R.¹

29
- 0037124885
- Angew. Chem. Int. Ed. 2002, 41, 2008-2022
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2008-2022

30
- 4344566130
- B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837.
- (2004) J. Org. Chem. , vol.69 , pp. 5813-5837
- Trost, B.M.¹

31
- 0020856030
- D. Seebach, A. K. Beck, M. Schiess, L. Widler, A. Wonnacott, Pure Appl. Chem. 1983, 55, 1807-1822
- (1983) Pure Appl. Chem. , vol.55 , pp. 1807-1822
- Seebach, D.¹ Beck, A.K.² Schiess, M.³ Widler, L.⁴ Wonnacott, A.⁵

32
- 84987490954
- D. Seebach, A. K. Beck, R. Imwinkelried, S. Roggo, A. Wonnacott, Helv. Chim. Acta 1987, 70, 954-974
- (1987) Helv. Chim. Acta , vol.70 , pp. 954-974
- Seebach, D.¹ Beck, A.K.² Imwinkelried, R.³ Roggo, S.⁴ Wonnacott, A.⁵

33
- 52349086352
- H. Pellissier, Tetrahedron 2008, 64, 10279-10317.
- (2008) Tetrahedron , vol.64 , pp. 10279-10317
- Pellissier, H.¹

34
- 0031759777
- T. Hintermann, D. Seebach, Helv. Chim. Acta 1998, 81, 2093-2126
- (1998) Helv. Chim. Acta , vol.81 , pp. 2093-2126
- Hintermann, T.¹ Seebach, D.²

35
- 0036293584
- C. Gaul, B. W. Schweizer, P. Seiler, D. Seebach, Helv. Chim. Acta 2002, 85, 1546-1566.
- (2002) Helv. Chim. Acta , vol.85 , pp. 1546-1566
- Gaul, C.¹ Schweizer, B.W.² Seiler, P.³ Seebach, D.⁴

36
- 34748812878
- R. Gõmez Arrayás, J. Adrio, J. C. Carretero, Angew. Chem. 2006, 118, 7836-7878
- (2006) Angew. Chem. , vol.118 , pp. 7836-7878
- Gõmez Arrayás, R.¹ Adrio, J.² Carretero, J.C.³

37
- 33845320520
- Angew. Chem. Int. Ed. 2006, 45, 7674-7715.
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7674-7715

38
- 84865318091
- For a leading and important discussion about the "geminal- diaryl" effect for conformational fixation and stereodirection in these structures, see:, M. Braun, Angew. Chem. 2012, 124, 2600-2612
- (2012) Angew. Chem. , vol.124 , pp. 2600-2612
- Braun, M.¹

39
- 84858048951
- Angew. Chem. Int. Ed. 2012, 51, 2550-2562; for the diaryl effect and its importance in organocatalysis, see
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2550-2562

40
- 67749104763
- U. GrosÄlj, D. Seebach, D. M. Badine, W. B. Schweizer, A. K. Beck, I. Krossing, P. Klose, Y. Hayashi, T. Uchimaru, Helv. Chim. Acta 2009, 92, 1225-1259.
- (2009) Helv. Chim. Acta , vol.92 , pp. 1225-1259
- Grosälj, U.¹ Seebach, D.² Badine, D.M.³ Schweizer, W.B.⁴ Beck, A.K.⁵ Krossing, I.⁶ Klose, P.⁷ Hayashi, Y.⁸ Uchimaru, T.⁹

41
- 4143138630
- For effective and powerful "organocatalysts" bearing a ferrocene moiety, see:, G. Fu, Acc. Chem. Res. 2004, 37, 542-547.
- (2004) Acc. Chem. Res. , vol.37 , pp. 542-547
- Fu, G.¹

42
- 84865455774
- E.-M. Tanzer, L. E. Zimmer, W. B. Schweizer, R. Gilmour, Chem. Eur. J. 2012, 18, 11334-11342
- (2012) Chem. Eur. J. , vol.18 , pp. 11334-11342
- Tanzer, E.-M.¹ Zimmer, L.E.² Schweizer, W.B.³ Gilmour, R.⁴

43
- 84856752517
- L. E. Zimmer, C. Sparr, R. Gilmour, Angew. Chem. 2011, 123, 12062-12074
- (2011) Angew. Chem. , vol.123 , pp. 12062-12074
- Zimmer, L.E.¹ Sparr, C.² Gilmour, R.³

44
- 83455243028
- Angew. Chem. Int. Ed. 2011, 50, 11860-11871.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 11860-11871

45
- 31144436331
- S. Coriani, A. Halaand, T. Helgaker, P. Jørgensen, ChemPhysChem 2006, 7, 245-249.
- (2006) ChemPhysChem , vol.7 , pp. 245-249
- Coriani, S.¹ Halaand, A.² Helgaker, T.³ Jørgensen, P.⁴

46
- 0031571441
- S. Top, B. Dauer, J. Vaissermann, G. Jaouen, J. Organomet. Chem. 1997, 541, 355-361.
- (1997) J. Organomet. Chem. , vol.541 , pp. 355-361
- Top, S.¹ Dauer, B.² Vaissermann, J.³ Jaouen, G.⁴

47
- 34250655385
- P. Vicennati, P. G. Cozzi, Eur. J. Org. Chem. 2007, 2248-2253.
- (2007) Eur. J. Org. Chem. , pp. 2248-2253
- Vicennati, P.¹ Cozzi, P.G.²

48
- 67651096136
- G. Falini, A. Gualandi, D. Savoia, Synthesis 2009, 2440-2446.
- (2009) Synthesis , pp. 2440-2446
- Falini, G.¹ Gualandi, A.² Savoia, D.³

49
- 0035030927
- M. Bandini, M. Gazzano, P. G. Cozzi, A. Umani-Ronchi, Eur. J. Org. Chem. 2001, 1937-1942.
- (2001) Eur. J. Org. Chem. , pp. 1937-1942
- Bandini, M.¹ Gazzano, M.² Cozzi, P.G.³ Umani-Ronchi, A.⁴

50
- 84861651997
- For a discussion about hydrolysis of amides, see:, J. Aubé, Angew. Chem. 2012, 124, 3117- 3119
- (2012) Angew. Chem. , vol.124 , pp. 3117-3119
- Aubé, J.¹

51
- 84858778418
- references therein
- Angew Chem. Int. Ed, 2012, 51, 3063-3065, and references therein.
- (2012) Angew Chem. Int. Ed , vol.51 , pp. 3063-3065

52
- 79955703354
- M. B. Schmid, K. Zeitler, R. M. Gschwind, J. Am. Chem. Soc. 2011, 133, 7065-7074
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7065-7074
- Schmid, M.B.¹ Zeitler, K.² Gschwind, R.M.³

53
- 80054704120
- M. B. Schmid, K. Zeitler, R. M. Gschwind, Chem. Sci. 2011, 2, 1793-1803.
- (2011) Chem. Sci. , vol.2 , pp. 1793-1803
- Schmid, M.B.¹ Zeitler, K.² Gschwind, R.M.³

54
- 77957190860
- For a highlight, see:, P. G. Cozzi, F. Benfatti, Angew. Chem. 2010, 122, 264-267
- (2010) Angew. Chem. , vol.122 , pp. 264-267
- Cozzi, P.G.¹ Benfatti, F.²

55
- 73349132694
- Angew. Chem. Int. Ed. 2010, 49, 256-259. See
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 256-259

56
- 70350454007
- P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. 2009, 121, 1339-1342
- (2009) Angew. Chem. , vol.121 , pp. 1339-1342
- Cozzi, P.G.¹ Benfatti, F.² Zoli, L.³

57
- 60149108649
- Angew. Chem. Int. Ed. 2009, 48, 1313-1316
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1313-1316

58
- 77957204396
- M. Guiteras Capdevila, F. Benfatti, L. Zoli, M. Stenta, P. G. Cozzi, Chem. Eur. J. 2010, 16, 11237-11241
- (2010) Chem. Eur. J. , vol.16 , pp. 11237-11241
- Guiteras Capdevila, M.¹ Benfatti, F.² Zoli, L.³ Stenta, M.⁴ Cozzi, P.G.⁵

59
- 80051747006
- A. Gualandi, E. Emer, M. Guiteras Capdevila, P. G. Cozzi, Angew. Chem. 2011, 123, 7988-7992
- (2011) Angew. Chem. , vol.123 , pp. 7988-7992
- Gualandi, A.¹ Emer, E.² Guiteras Capdevila, M.³ Cozzi, P.G.⁴

60
- 80051747006
- Angew. Chem. Int. Ed. 2011, 50, 7842-7846.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7842-7846

61
- 79953693620
- K. Motoyama, M. Ikeda, Y. Miyake, Y. Nishibayashi, Eur. J. Org. Chem. 2011, 2239-2246
- (2011) Eur. J. Org. Chem. , pp. 2239-2246
- Motoyama, K.¹ Ikeda, M.² Miyake, Y.³ Nishibayashi, Y.⁴

62
- 79959445802
- R. Sinisi, M. V. Vita, E. A. Gualandi, E. Emer, P. G. Cozzi, Chem. Eur. J. 2011, 17, 7404-7408.
- (2011) Chem. Eur. J. , vol.17 , pp. 7404-7408
- Sinisi, R.¹ Vita, M.V.² Gualandi, E.A.³ Emer, E.⁴ Cozzi, P.G.⁵

63
- 79955905485
- K. Patora-Komisarska, M. Benohoud, H. Ishikawa, D. Seebach, Y. Hayashi, Helv. Chim. Acta 2011, 94, 719-745
- (2011) Helv. Chim. Acta , vol.94 , pp. 719-745
- Patora-Komisarska, K.¹ Benohoud, M.² Ishikawa, H.³ Seebach, D.⁴ Hayashi, Y.⁵

64
- 79958780947
- J. Burès, A. Armstrong, D. G. Blackmond, J. Am. Chem. Soc. 2011, 133, 8822-8823
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 8822-8823
- Burès, J.¹ Armstrong, A.² Blackmond, D.G.³

65
- 84865845003
- G. Talavera, E. Reyes, J. L. Vicario, L. Carrillo, Angew. Chem. 2012, 124, 4180-4183
- (2012) Angew. Chem. , vol.124 , pp. 4180-4183
- Talavera, G.¹ Reyes, E.² Vicario, J.L.³ Carrillo, L.⁴

66
- 84859968475
- Angew. Chem. Int. Ed. 2012, 51, 4104-4107
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4104-4107

67
- 84876722258
- J. Duschmalé, J. Wiest, M. Wiesne, H. Wennemers, Chem. Science 2013, 4, 1312-1318
- (2013) Chem. Science , vol.4 , pp. 1312-1318
- Duschmalé, J.¹ Wiest, J.² Wiesne, M.³ Wennemers, H.⁴

68
- 84873927765
- G. Sahoo, H. Rahaman, A. Madarász, I. Pápai, M. Melarto, A. Valkonen, P. M. Pihko, Angew. Chem. 2012, 124, 13321-13325
- (2012) Angew. Chem. , vol.124 , pp. 13321-13325
- Sahoo, G.¹ Rahaman, H.² Madarász, A.³ Pápai, I.⁴ Melarto, M.⁵ Valkonen, A.⁶ Pihko, P.M.⁷

69
- 84871982716
- Angew. Chem. Int. Ed. 2012, 51, 13144-13148; for a highlight, see
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 13144-13148

70
- 84878061590
- C. Moberg, Angew. Chem. 2013, 125, 2214-2216
- (2013) Angew. Chem. , vol.125 , pp. 2214-2216
- Moberg, C.¹

71
- 84873904037
- Angew. Chem. Int. Ed. 2013, 52, 2160-2162.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 2160-2162

72
- 84871087296
- Recently, constrained pyrrolidine catalysts, in which the rigidity of the bicyclic structure imposes a synclinal endo disposition of the bulky substituents with respect to the pyrrolidine ring, were described, see
- Recently, constrained pyrrolidine catalysts, in which the rigidity of the bicyclic structure imposes a synclinal endo disposition of the bulky substituents with respect to the pyrrolidine ring, were described, see:, M. Lombardo, A. Quintavalla, E. Montroni, C. Trombini, Adv. Synth. Catal. 2012, 354, 3428-3443.
- (2012) Adv. Synth. Catal. , vol.354 , pp. 3428-3443
- Lombardo, M.¹ Quintavalla, A.² Montroni, E.³ Trombini, C.⁴

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