SCOPUS 정보 검색 플랫폼

Volumn , Issue 13, 2007, Pages 2037-2040

Synthesis of trans-3-substituted cyclohexylamines via Brønsted acid catalyzed and substrate-mediated triple organocatalytic cascade reaction

(2) Zhou, Jian a List, Benjamin a

a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG (Germany)

Author keywords

3 substituted cyclohexyl amine; Organocatalysis; Organocatalytic cascade reaction; Substrate co catalyzed

Indexed keywords

AMINE; BRONSTED ACID; CYCLOHEXYLAMINE DERIVATIVE; ENAMINE;

ALDOL REACTION; AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34548184965 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984877 Document Type: Article

Times cited : (20)

References (50)

1
- 17144366282
- For leading reviews, see: a
- For leading reviews, see: (a) Ramón, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1602
- Ramón, D.J.¹ Yus, M.²

2
- 0037423972
- (b) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
- (2003) Chem. Commun , pp. 551
- Nicolaou, K.C.¹ Montagnon, T.² Snyder, S.A.³

3
- 7044235263
- (c) Tietze, L. F. Chem. Rev. 1996, 96, 115.
- (1996) Chem. Rev , vol.96 , pp. 115
- Tietze, L.F.¹

4
- 17444401687
- (d) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
- (2005) Chem. Rev , vol.105 , pp. 1001
- Wasilke, J.-C.¹ Obrey, S.J.² Baker, R.T.³ Bazan, G.C.⁴

5
- 33947198541
- For an excellent review, see
- For an excellent review, see: Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem. Int. Ed. 2007, 46, 1570.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1570
- Enders, D.¹ Grondal, C.² Hüttl, M.R.M.³

6
- 33748766864
- For important reviews, see: a
- For important reviews, see: (a) List, B.; Yang, J. W. Science 2006, 313, 1584.
- (2006) Science , vol.313 , pp. 1584
- List, B.¹ Yang, J.W.²

7
- 15244343428
- (b) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
- (2005) Org. Biomol. Chem , vol.3 , pp. 719
- Seayad, J.¹ List, B.²

8
- 6044269452
- (c) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5138
- Dalko, P.I.¹ Moisan, L.²

9
- 32844457119
- (a) List, B. Chem. Commun. 2006, 819.
- (2006) Chem. Commun , pp. 819
- List, B.¹

10
- 33745715054
- (b) 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

11
- 33845505476
- (c) 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

12
- 27544489337
- For recent examples, see: a
- For recent examples, see: (a) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 15036
- Yang, J.W.¹ Hechavarria Fonseca, M.T.² List, B.³

13
- 27544485685
- (b) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 15051
- Huang, Y.¹ Walji, A.M.² Larsen, C.H.³ MacMillan, D.W.C.⁴

14
- 27844440320
- (c) Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 15710
- Marigo, M.¹ Schulte, T.² Franzén, J.³ Jørgensen, K.A.⁴

15
- 33745211429
- (d) Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature (London) 2006, 441, 861.
- (2006) Nature (London) , vol.441 , pp. 861
- Enders, D.¹ Hüttl, M.R.M.² Grondal, C.³ Raabe, G.⁴

16
- 33747594792
- (e) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 10354
- Wang, W.¹ Li, H.² Wang, J.³ Zu, L.⁴

17
- 33845190114
- (f) Brandau, S.; Maerten, E.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 14986
- Brandau, S.¹ Maerten, E.² Jørgensen, K.A.³

18
- 33846429586
- (g) Enders, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem. Int. Ed. 2007, 46, 467.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 467
- Enders, D.¹ Hüttl, M.R.M.² Runsink, J.³ Raabe, G.⁴ Wendt, B.⁵

19
- 34248192461
- (h) Carlone, A.; Cabrera, S.; Marigo, M.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2007, 46, 1101.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1101
- Carlone, A.¹ Cabrera, S.² Marigo, M.³ Jørgensen, K.A.⁴

20
- 33846528479
- (i) Li, H.; Wang, J.; E-Nunu, T.; Zu, L.; Jiang, W.; Wei, S.; Wang, W. Chem. Commun. 2007, 507.
- (2007) Chem. Commun , pp. 507
- Li, H.¹ Wang, J.² E-Nunu, T.³ Zu, L.⁴ Jiang, W.⁵ Wei, S.⁶ Wang, W.⁷

21
- 33646468489
- For reviews, see: a
- For reviews, see: (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1520
- Taylor, M.S.¹ Jacobsen, E.N.²

22
- 33745683617
- (b) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
- (2006) Adv. Synth. Catal , vol.348 , pp. 999
- Akiyama, T.¹ Itoh, J.² Fuchibe, K.³

23
- 33746272976
- (c) Connon, S. J. Angew. Chem. Int. Ed. 2006, 45, 3909.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3909
- Connon, S.J.¹

24
- 29844448114
- (d) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
- (2005) Org. Biomol. Chem , vol.3 , pp. 4299
- Takemoto, Y.¹

25
- 17044380275
- (e) Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem. Int. Ed. 2005, 44, 1758.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1758
- Bolm, C.¹ Rantanen, T.² Schiffers, I.³ Zani, L.⁴

26
- 0346865819
- (f) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
- (2003) Chem. Soc. Rev , vol.32 , pp. 289
- Schreiner, P.R.¹

27
- 33746286405
- (a) Mayer, S.; List, B. Angew. Chem. Int. Ed. 2006, 45, 4193.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 4193
- Mayer, S.¹ List, B.²

28
- 33750084396
- (b) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13368
- Martin, N.J.A.¹ List, B.²

29
- 10944220196
- For chiral amine-catalyzed conjugate reductions of α,β- unsaturated carbonyl compounds, see: a
- For chiral amine-catalyzed conjugate reductions of α,β- unsaturated carbonyl compounds, see: (a) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem. Int. Ed. 2004, 43, 6660.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 6660
- Yang, J.W.¹ Hechavarria Fonseca, M.T.² List, B.³

30
- 11244320360
- (b) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem. Int. Ed. 2005, 44, 108.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 108
- Yang, J.W.¹ Hechavarria Fonseca, M.T.² Vignola, N.³ List, B.⁴

31
- 11844277087
- (c) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 32
- Ouellet, S.G.¹ Tuttle, J.B.² MacMillan, D.W.C.³

32
- 33749516633
- (d) Tutlle, J. B.; Ouellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 12662
- Tutlle, J.B.¹ Ouellet, S.G.² MacMillan, D.W.C.³

33
- 28044438742
- (a) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem. Int. Ed. 2005, 44, 7424.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 7424
- Hoffmann, S.¹ Seayad, A.M.² List, B.³

34
- 33749534513
- (b) Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13074
- Hoffmann, S.¹ Nicoletti, M.² List, B.³

35
- 24044465512
- Also see: c
- Also see: (c) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.
- (2005) Org. Lett , vol.7 , pp. 3781
- Rueping, M.¹ Sugiono, E.² Azap, C.³ Theissmann, T.⁴ Bolte, M.⁵

36
- 30744477746
- (d) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 84
- Storer, R.I.¹ Carrera, D.E.² Ni, Y.³ MacMillan, D.W.C.⁴

37
- 33746269442
- For the reduction of quinolines, benzoxazines, benzothiazines, and benzoxazinones, see: e
- For the reduction of quinolines, benzoxazines, benzothiazines, and benzoxazinones, see: (e) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 3683.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3683
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

38
- 33750148995
- (f) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 6751.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6751
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

39
- 25444480017
- For achiral version, see: g
- For achiral version, see: (g) Rueping, M.; Azap, C.; Sugiono, E.; Theissmann, T. Synlett 2005, 2367.
- (2005) Synlett , pp. 2367
- Rueping, M.¹ Azap, C.² Sugiono, E.³ Theissmann, T.⁴

40
- 33646574664
- (h) Rueping, M.; Theissmann, T.; Antonchick, A. P. Synlett 2006, 1071.
- (2006) Synlett , pp. 1071
- Rueping, M.¹ Theissmann, T.² Antonchick, A.P.³

41
- 13644256524
- For a review on amine-catalyzed aldol reactions, see:, Mahrwald, R, Ed, Wiley-VCH: Weinhein Germany
- For a review on amine-catalyzed aldol reactions, see: List, B. In Modern Aldol Reactions, Vol. 1; Mahrwald, R., Ed.; Wiley-VCH: Weinhein Germany, 2004, 161-200.
- (2004) Modern Aldol Reactions , vol.1 , pp. 161-200
- List, B.¹

42
- 33344455013
- For a recent nonasymmetric amine mediated aldol condensation, Pd-catalyzed hydrogenation-reductive amination cascade in the synthesis of Fenpropimorph, see
- For a recent nonasymmetric amine mediated aldol condensation, Pd-catalyzed hydrogenation-reductive amination cascade in the synthesis of Fenpropimorph, see: Forsyth, S. A.; Gunaratne, H. Q. N.; Hardacre, C.; McKeown, A.; Rooney, D. W. Org. Process Res. Dev. 2006, 10, 94.
- (2006) Org. Process Res. Dev , vol.10 , pp. 94
- Forsyth, S.A.¹ Gunaratne, H.Q.N.² Hardacre, C.³ McKeown, A.⁴ Rooney, D.W.⁵

43
- 34250835001
- For the determination of the relative configuration and a highly enantioselective synthesis of the corresponding cis-products, see: Zhou, J, List, B. J. Am. Chem. Soc. 2007, 129, 7498
- For the determination of the relative configuration and a highly enantioselective synthesis of the corresponding cis-products, see: Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498.

44
- 34548189754
- Typical Procedure: To a Schlenk tube was added 2,6-dione 1 (0.2 mmol, p-ethoxyphenyl amine 2 (0.3 mmol, Hantzsch ester 3 (0.45 mmol) and PTSA·H2O (2 mg, 0.01 mmol, and then charged with argon, followed by adding MS 5 Å (50 mg) and anhyd toluene (0.5 mL, The mixture was stirred at 40°C for 24-72 h. To determine the ratio of trans- to cis-product, 20 μL of the reaction mixture was taken for GC-MS analysis, or 0.2 mL of crude mixture for 1H NMR analysis. The sample for analysis and the rest were emerged together for column chromatography purification using hexane-EtOAc (96:4) or CH2CT 2 as eluent. Compound trans-4a was obtained as colorless liquid (0.144 mmol, 72, after chromatography with hexane-EtOAc (96:4, 1H NMR (300 MHz, CDCl3, δ, 0.91 (d, J, 6.4 Hz, 3 H, 0.99-1.10 (m, 1 H, 1.27-1.37 (m, 1 H, 1.36 t, J, 6.9 Hz
- +: 234.1852; found: 234.1852.

45
- 0342867567
- This is in contrast to the corresponding NaOH-catalyzed cyclization of 2,6-heptanediones, see: Danishefsky, S, Zimmer, A. J. Org. Chem. 1976, 41, 4059
- This is in contrast to the corresponding NaOH-catalyzed cyclization of 2,6-heptanediones, see: Danishefsky, S.; Zimmer, A. J. Org. Chem. 1976, 41, 4059.

46
- 0018427167
- For a related investigation, see
- For a related investigation, see: De Nie-Sarink, M. J.; Pandit, U. K. Tetrahedron Lett. 1979, 26, 2449.
- (1979) Tetrahedron Lett , vol.26 , pp. 2449
- De Nie-Sarink, M.J.¹ Pandit, U.K.²

47
- 33749511797
- Verkade, J. M. M.; van Hermert, L. J. C.; Quaedflieg, P. J. L. M.; Alsters, P. L.; van Delft, F. L.; Rutjes, F. P. J. T. Tetrahedron Lett. 2006, 47, 8109.
- (2006) Tetrahedron Lett , vol.47 , pp. 8109
- Verkade, J.M.M.¹ van Hermert, L.J.C.² Quaedflieg, P.J.L.M.³ Alsters, P.L.⁴ van Delft, F.L.⁵ Rutjes, F.P.J.T.⁶

48
- 0017339896
- Based on a SciFinder survey, there are more than 300 patented structures containing a 3-methylcyclohexylamine moiety. For selected pharmaceutically active compounds incorporating a 3-substituted cyclohexylamine, see: (a) Johnston, T. P.; McCaleb, G. S.; Clayton, S. D.; Frye, J. L.; Krauth, C. A.; Montgomery, J. A. J. Med. Chem. 1977, 20, 279.
- Based on a SciFinder survey, there are more than 300 patented structures containing a 3-methylcyclohexylamine moiety. For selected pharmaceutically active compounds incorporating a 3-substituted cyclohexylamine, see: (a) Johnston, T. P.; McCaleb, G. S.; Clayton, S. D.; Frye, J. L.; Krauth, C. A.; Montgomery, J. A. J. Med. Chem. 1977, 20, 279.

49
- 19244379420
- (b) Palomba, M.; Pau, A.; Boatto, G.; Asproni, B.; Auzzas, L.; Cerri, R.; Arenare, L.; Filippelli, W.; Falcone, G.; Motola, G. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 17.
- (2000) Arch. Pharm. Pharm. Med. Chem , vol.333 , pp. 17
- Palomba, M.¹ Pau, A.² Boatto, G.³ Asproni, B.⁴ Auzzas, L.⁵ Cerri, R.⁶ Arenare, L.⁷ Filippelli, W.⁸ Falcone, G.⁹ Motola, G.¹⁰

50
- 27644591577
- (c) Norman, B. H.; Lander, P. A.; Gruber, J. M.; Kroin, J. S.; Cohen, J. D.; Jungheim, L. N.; Starling, J. J.; Law, K. L.; Self, T. D.; Tabas, L. B.; Williams, D. C.; Paul, D. C.; Dantzig, A. H. Bioorg. Med. Chem. Lett. 2005, 15, 5526.
- (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 5526
- Norman, B.H.¹ Lander, P.A.² Gruber, J.M.³ Kroin, J.S.⁴ Cohen, J.D.⁵ Jungheim, L.N.⁶ Starling, J.J.⁷ Law, K.L.⁸ Self, T.D.⁹ Tabas, L.B.¹⁰ Williams, D.C.¹¹ Paul, D.C.¹² Dantzig, A.H.¹³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.