SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 6, 2007, Pages 885-888

Organocatalytic asymmetric conjugate nucleophilic glyoxylation

(3) Enders, Dieter a Bonten, Maurice Hubert a Raabe, Gerhard a

a RWTH AACHEN UNIVERSITY (Germany)

Author keywords

Aminonitriles; Glyoxylation; Iminium activation; Organocatalysis; Umpolung

Indexed keywords

ESTER DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; GLYOXYLATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 34247111301 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970787 Document Type: Article

Times cited : (30)

References (67)

1
- 0003433653
- Pergamon Press: New York
- (a) Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983.
- (1983) Total Synthesis of Natural Products: The Chiron Approach
- Hanessian, S.¹

2
- 0344875710
- (b) Nakamura, S.; Hirata, Y.; Kurosaki, T.; Anada, M.; Kataoka, O.; Kitagaki, S.; Hashimoto, S. Angew. Chem. Int. Ed. 2003, 42, 5351.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 5351
- Nakamura, S.¹ Hirata, Y.² Kurosaki, T.³ Anada, M.⁴ Kataoka, O.⁵ Kitagaki, S.⁶ Hashimoto, S.⁷

3
- 1842787730
- (c) Rodrigues, J. A. R.; Moran, P. J. S.; Milagre, C. D. F.; Ursini, C. V. Tetrahedron Lett. 2004, 45, 3579.
- (2004) Tetrahedron Lett , vol.45 , pp. 3579
- Rodrigues, J.A.R.¹ Moran, P.J.S.² Milagre, C.D.F.³ Ursini, C.V.⁴

4
- 29444451549
- (d) Pollex, A.; Hiersemann, M. Org. Lett. 2005, 7, 5705.
- (2005) Org. Lett , vol.7 , pp. 5705
- Pollex, A.¹ Hiersemann, M.²

5
- 0003438149
- John Wiley and Sons: New York
- (a) Dewick, P. M. Medicinal Natural Products; John Wiley and Sons: New York, 1997, 147.
- (1997) Medicinal Natural Products , pp. 147
- Dewick, P.M.¹

6
- 0004214314
- Churchill Livingstone: New York
- (b) Marshall, W. J.; Bangert, S. K. Clinical Biochemistry; Churchill Livingstone: New York, 1995, 611.
- (1995) Clinical Biochemistry , pp. 611
- Marshall, W.J.¹ Bangert, S.K.²

7
- 0026563021
- (a) Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451.
- (1992) Med. Chem , vol.35 , pp. 451
- Ocain, T.D.¹ Rich, D.H.J.²

8
- 0027172371
- Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo, E. W. J Med. Chem. 1993, 36, 2431.
- (b) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo, E. W. J Med. Chem. 1993, 36, 2431.

9
- 0037179611
- (c) Adang, A. E. P.; de Man, A. P. A.; Vogel, G. M. T.; Grootenhuis, P. D. J.; Smit, M. J.; Peters, C. A. M.; Visser, A.; Rewinkel, J. B. M.; van Dinther, T.; Lucas, H.; Kelder, J.; van Aelst, S.; Meuleman, D. G.; van Boeckel, C. A. A. J. Med. Chem. 2002, 45, 4419.
- (2002) Med. Chem , vol.45 , pp. 4419
- Adang, A.E.P.¹ de Man, A.P.A.² Vogel, G.M.T.³ Grootenhuis, P.D.J.⁴ Smit, M.J.⁵ Peters, C.A.M.⁶ Visser, A.⁷ Rewinkel, J.B.M.⁸ van Dinther, T.⁹ Lucas, H.¹⁰ Kelder, J.¹¹ van Aelst, S.¹² Meuleman, D.G.¹³ van Boeckel, C.A.A.J.¹⁴

10
- 0010392869
- (a) Yuan, W.; Wong, C.-H.; Haeggström, J. Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552.
- (1992) Am. Chem. Soc , vol.114 , pp. 6552
- Yuan, W.¹ Wong, C.-H.² Haeggström, J.Z.³ Wetterholm, A.⁴ Samuelsson, B.J.⁵

11
- 0027457065
- (b) Yuan, W.; Munoz, B.; Wong, C.-H.; Haeggström, J. Z.; Wetterholm, A.; Samuelsson, B. J. Med. Chem. 1993, 36, 211.
- (1993) J. Med. Chem , vol.36 , pp. 211
- Yuan, W.¹ Munoz, B.² Wong, C.-H.³ Haeggström, J.Z.⁴ Wetterholm, A.⁵ Samuelsson, B.⁶

12
- 0005752673
- Berzelius, J. J. Ann. Phys. 1835, 36, 1.
- (1835) Ann. Phys , vol.36 , pp. 1
- Berzelius, J.J.¹

13
- 33845552242
- Reviews: a
- Reviews: (a) Cooper, A. J. L.; Ginos, J. Z.; Meister, A. Chem. Rev. 1983, 83, 321.
- (1983) Chem. Rev , vol.83 , pp. 321
- Cooper, A.J.L.¹ Ginos, J.Z.² Meister, A.³

14
- 0000353319
- (b) Kovacs, L. Recl. Trav. Chim. Pays-Bas 1993, 112, 471.
- (1993) Recl. Trav. Chim. Pays-Bas , vol.112 , pp. 471
- Kovacs, L.¹

15
- 0026661322
- (a) Enders, D.; Dyker, H.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 618.
- (1992) Angew. Chem., Int. Ed. Engl , vol.31 , pp. 618
- Enders, D.¹ Dyker, H.² Raabe, G.³

16
- 33748216784
- (b) Enders, D.; Dyker, H.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 421.
- (1993) Angew. Chem., Int. Ed. Engl , vol.32 , pp. 421
- Enders, D.¹ Dyker, H.² Raabe, G.³

17
- 0031976717
- (c) Enders, D.; Dyker, H.; Leusink, F. R. Chem. Eur. J. 1998, 4, 311.
- (1998) Chem. Eur. J , vol.4 , pp. 311
- Enders, D.¹ Dyker, H.² Leusink, F.R.³

18
- 0036062739
- Tyrell, E.; Skinner, G. A.; Janes, J.; Milsom, G. Synlett 2002, 1073.
- (2002) Synlett , pp. 1073
- Tyrell, E.¹ Skinner, G.A.² Janes, J.³ Milsom, G.⁴

19
- 7044286189
- (a) Abraham, L.; Körner, M.; Schwab, P.; Hiersemann, M. Adv. Synth. Catal. 2004, 346, 1281.
- (2004) Adv. Synth. Catal , vol.346 , pp. 1281
- Abraham, L.¹ Körner, M.² Schwab, P.³ Hiersemann, M.⁴

20
- 1842635738
- (b) Abraham, L.; Körner, M.; Hiersemann, M. Tetrahedron Lett. 2004, 45, 3647.
- (2004) Tetrahedron Lett , vol.45 , pp. 3647
- Abraham, L.¹ Körner, M.² Hiersemann, M.³

21
- 47749122232
- Berkessel, A, Gröger, H, Eds, Wiley-VCH: Weinheim
- (a) Asymmetric Organocatalysis; Berkessel, A.; Gröger, H., Eds.; Wiley-VCH: Weinheim, 2005.
- (2005) Asymmetric Organocatalysis

22
- 6044269452
- (b) Dalko, P. I.; Moinsan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5138
- Dalko, P.I.¹ Moinsan, L.²

23
- 15244343428
- (c) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
- (2005) Org. Biomol. Chem , vol.3 , pp. 719
- Seayad, J.¹ List, B.²

24
- 33745715054
- Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79.
- (2006) Aldrichimica Acta , vol.39 , pp. 79
- Lelais, G.¹ MacMillan, D.W.C.²

25
- 0034807741
- (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 4370
- Paras, N.A.¹ MacMillan, D.W.C.²

26
- 0037138701
- (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 1172
- Austin, J.F.¹ MacMillan, D.W.C.²

27
- 0037055106
- (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 7894
- Paras, N.A.¹ MacMillan, D.W.C.²

28
- 0037419866
- (d) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J Am. Chem. Soc. 2003, 125, 1192.
- (2003) Am. Chem. Soc , vol.125 , pp. 1192
- Brown, S.P.¹ Goodwin, N.C.² MacMillan, D.W.C.J.³

29
- 24944514433
- (a) Prieto, A.; Halland, N.; Jorgensen, K. A. Org. Lett. 2005, 7, 3897.
- (2005) Org. Lett , vol.7 , pp. 3897
- Prieto, A.¹ Halland, N.² Jorgensen, K.A.³

30
- 33645454505
- (b) Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V. Chem. Commun. 2006, 66.
- (2006) Chem. Commun , pp. 66
- Knudsen, K.R.¹ Mitchell, C.E.T.² Ley, S.V.³

31
- 33750440775
- Gotoh, H.; Masui, R.; Ogino, H.; Shoji, M.; Hayashi, Y. Angew. Chem. Int. Ed. 2006, 45, 6853.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6853
- Gotoh, H.¹ Masui, R.² Ogino, H.³ Shoji, M.⁴ Hayashi, Y.⁵

32
- 34250374484
- Enders, D.; Bonten, M. H.; Raabe, G. Angew. Chem., Int. Ed. 2001, 46, 2314.
- (2001) Angew. Chem., Int. Ed , vol.46 , pp. 2314
- Enders, D.¹ Bonten, M.H.² Raabe, G.³

33
- 84981810671
- (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1969, 8, 639.
- (1969) Angew. Chem., Int. Ed. Engl , vol.8 , pp. 639
- Seebach, D.¹

34
- 0002639647
- (b) Seebach, D. Synthesis 1969, 17.
- (1969) Synthesis , pp. 17
- Seebach, D.¹

35
- 0141725892
- (a) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204.
- (2003) Am. Chem. Soc , vol.125 , pp. 11204
- Taylor, M.S.¹ Jacobsen, E.N.J.²

36
- 33744805367
- (b) Balskus, E. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 6810.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 6810
- Balskus, E.P.¹ Jacobsen, E.N.²

37
- 18844456337
- (c) Poulsen, T. B.; Alemparte, C.; Saabe, S.; Bella, M.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2005, 44, 2896.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 2896
- Poulsen, T.B.¹ Alemparte, C.² Saabe, S.³ Bella, M.⁴ Jørgensen, K.A.⁵

38
- 21244480844
- (d) Li, H.; Song, J.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 8948
- Li, H.¹ Song, J.² Liu, X.³ Deng, L.⁴

39
- 33746280588
- (e) Wu, F.; Hong, R.; Khan, J.; Liu, X.; Deng, L. Angew. Chem. Int. Ed. 2006, 45, 4301.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 4301
- Wu, F.¹ Hong, R.² Khan, J.³ Liu, X.⁴ Deng, L.⁵

40
- 18744407280
- (a) Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6954.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 6954
- Marigo, M.¹ Franzén, J.² Poulsen, T.B.³ Zhuang, W.⁴ Jorgensen, K.A.⁵

41
- 29844457732
- (b) Frenzén, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjærsgaard, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 18296
- Frenzén, J.¹ Marigo, M.² Fielenbach, D.³ Wabnitz, T.C.⁴ Kjærsgaard, A.⁵ Jørgensen, K.A.⁶

42
- 22144459070
- (c) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem. Int. Ed. 2005, 44, 4212.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4212
- Hayashi, Y.¹ Gotoh, H.² Hayashi, T.³ Shoji, M.⁴

43
- 25444470782
- (d) Chi, Y.; Gellman, S. H. Org. Lett. 2005, 7, 4253.
- (2005) Org. Lett , vol.7 , pp. 4253
- Chi, Y.¹ Gellman, S.H.²

44
- 33845505476
- Review
- (e) Review: Palomo, C.; Mielgo, A. Angew. Chem. Int. Ed. 2006, 45, 7876.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7876
- Palomo, C.¹ Mielgo, A.²

45
- 33745211429
- Enders, D.; Hüttl, M. R. M.; Grondai, C.; Raabe, G. Nature (London) 2006, 441, 861.
- (2006) Nature (London) , vol.441 , pp. 861
- Enders, D.¹ Hüttl, M.R.M.² Grondai, C.³ Raabe, G.⁴

46
- 84988058551
- (a) Enders, D.; Kipphardt, H.; Gerdes, P.; Breña-Valle, L. J.; Bhushan, V. Bull. Soc. Chim. Belg. 1988, 97, 691.
- (1988) Bull. Soc. Chim. Belg , vol.97 , pp. 691
- Enders, D.¹ Kipphardt, H.² Gerdes, P.³ Breña-Valle, L.J.⁴ Bhushan, V.⁵

47
- 29844457732
- (b) Frenzén, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjaersgaard, A.; Jergensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 18296
- Frenzén, J.¹ Marigo, M.² Fielenbach, D.³ Wabnitz, T.C.⁴ Kjaersgaard, A.⁵ Jergensen, K.A.⁶

48
- 0002988180
- Enders, D.; Dyker, H.; Raabe, G.; Runsink, J. Synlett 1992, 901.
- (1992) Synlett , pp. 901
- Enders, D.¹ Dyker, H.² Raabe, G.³ Runsink, J.⁴

49
- 37049079385
- (a) Bunnage, M. E.; Chernega, A. N.; Davies, S. G.; Goodwin, J. C. J. Chem. Soc., Perkin Trans. 1 1994, 2373.
- (1994) Chem. Soc., Perkin Trans. 1 , pp. 2373
- Bunnage, M.E.¹ Chernega, A.N.² Davies, S.G.³ Goodwin, J.C.J.⁴

50
- 2942644316
- (b) Davies, S. G.; Hughes, D. G.; Nicholson, R. L.; Smith, A. D.; Wright, A. J. Org. Biomol. Chem. 2004, 2, 1549.
- (2004) Org. Biomol. Chem , vol.2 , pp. 1549
- Davies, S.G.¹ Hughes, D.G.² Nicholson, R.L.³ Smith, A.D.⁴ Wright, A.J.⁵

51
- 84877935319
- These data can be obtained free of charge from the Cambridge Crystallographic Data Center via
- CCDC 631143 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
- CCDC 631143 contains the supplementary crystallographic data for this paper

52
- 0000782851
- (a) Enders, D.; Lotter, H. Nouv. J. Chim. 1984, 8, 747.
- (1984) Nouv. J. Chim , vol.8 , pp. 747
- Enders, D.¹ Lotter, H.²

53
- 84945031738
- (b) Raabe, G.; Zobel, E.; Fleischhauer, J.; Gerdes, P.; Mannes, D.; Müller, E.; Enders, D. Z. Naturforsch., A: Phys. Sci. 1991, 46, 275.
- (1991) Z. Naturforsch., A: Phys. Sci , vol.46 , pp. 275
- Raabe, G.¹ Zobel, E.² Fleischhauer, J.³ Gerdes, P.⁴ Mannes, D.⁵ Müller, E.⁶ Enders, D.⁷

54
- 84987338503
- (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837.
- (1992) Synlett , pp. 837
- Enders, D.¹ Mannes, D.² Raabe, G.³

55
- 0029015249
- (d) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659.
- (1995) Synthesis , pp. 659
- Enders, D.¹ Kirchhoff, J.² Mannes, D.³ Raabe, G.⁴

56
- 33749284233
- (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361.
- (1996) Liebigs Ann , pp. 1361
- Enders, D.¹ Kirchhoff, J.² Lausberg, V.³

57
- 2842568219
- (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem. 1998, 63.
- (1998) Eur. J. Org. Chem , pp. 63
- Enders, D.¹ Kirchhoff, J.² Gerdes, P.³ Mannes, D.⁴ Raabe, G.⁵ Runsink, J.⁶ Boche, G.⁷ Marsch, M.⁸ Ahlbrecht, H.⁹ Sommer, H.¹⁰

58
- 0002861359
- (g) Enders, D.; Shilvock, J. P.; Raabe, G. J. Chem. Soc., Perkin Trans. 1 1999, 1617.
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1617
- Enders, D.¹ Shilvock, J.P.² Raabe, G.³

59
- 0034400108
- (h) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359.
- (2000) Chem. Soc. Rev , vol.29 , pp. 359
- Enders, D.¹ Shilvock, J.P.²

60
- 0036193542
- (i) Enders, D.; Lausberg, V.; Signore, G. D.; Berner, O. M. Synthesis 2002, 4, 515.
- (2002) Synthesis , vol.4 , pp. 515
- Enders, D.¹ Lausberg, V.² Signore, G.D.³ Berner, O.M.⁴

61
- 0141991211
- (j) Enders, D.; Moser, M. Tetrahedron Lett. 2003, 44, 8479.
- (2003) Tetrahedron Lett , vol.44 , pp. 8479
- Enders, D.¹ Moser, M.²

62
- 0037974203
- (k) Enders, D.; Signore, G. D.; Berner, O. M. Chirality 2003, 15, 510.
- (2003) Chirality , vol.15 , pp. 510
- Enders, D.¹ Signore, G.D.² Berner, O.M.³

63
- 0041378065
- (l) Gröger, H. Chem. Rev. 2003, 103, 2795.
- (2003) Chem. Rev , vol.103 , pp. 2795
- Gröger, H.¹

64
- 19844382868
- (m) Enders, D.; Milovanovic, M.; Voloshina, E.; Raabe, G.; Fleischhauer, J. Eur. J. Org. Chem. 2005, 1984.
- (1984) Eur. J. Org. Chem , vol.2005
- Enders, D.¹ Milovanovic, M.² Voloshina, E.³ Raabe, G.⁴ Fleischhauer, J.⁵

65
- 35648936932
- (n) Enders, D.; Milovanovic, M. Z. Naturforsch., B: Chem. Sci. 2007, 62, 117.
- (2007) Z. Naturforsch., B: Chem. Sci , vol.62 , pp. 117
- Enders, D.¹ Milovanovic, M.²

66
- 33746470627
- Introduction of the Cyanide Group by Addition to C=O
- Murahashi, S.-I, Ed, Georg Thieme Verlag: Stuttgart
- (o) North, M. Introduction of the Cyanide Group by Addition to C=O, In Science of Synthesis, Vol. 19; Murahashi, S.-I., Ed.; Georg Thieme Verlag: Stuttgart, 2004, 285.
- (2004) Science of Synthesis , vol.19 , pp. 285
- North, M.¹

67
- 34247125016
- All new compounds were fully characterised (IR, NMR, MS, elemental analysis, optical rotation, melting point, Organocatalytic Asymmetric Nucleophilic Glyoxylation to 8a, Typical Procedure To a solution of the aminonitrile 1 (840 mg, 4 mmol) in toluene (4.0 mL) were added the aldehyde 3a (280 mg, 0.33 mL, 4 mmol) and the catalyst (S)-2 (293 mg, 20 mol, The reaction mixture was stirred at r.t. for 2 d, quenched with brine and extracted three times with Et2O (10 mL, The organic layer was dried over MgSO4 and concentrated in vacuo. The crude product 4a was dissolved in anhyd THF (8.0 mL, cooled to 0°C and NaBH4 (453 mg, 12 mmol) was added. The suspension was slowly treated with MeOH (2 mL, using a syringe pump. After stirring for 1 h, the mixture was quenched with sat. NH4Cl solution, the organic phase separated and the aqueous phase extracted three times with Et2O 10 mL, The combi
- 4Si: C, 60.72; H, 10.19. Found: C, 60.91; H, 10.08.

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