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Synlett

Volumn , Issue 9, 2007, Pages 1455-1457

Thiourea-catalyzed transfer hydrogenation of aldimines

(2) Zhang, Zhiguo a Schreiner, Peter R a

a JUSTUS LIEBIG UNIVERSITY (Germany)

Author keywords

Hantzsch dihydropyridine; Hydrogen bonds; Organo catalysis; Thiourea; Transfer hydrogenation

Indexed keywords

1,4 DIHYDROPYRIDINE; ALDIMINE DERIVATIVE; IMINE; THIOUREA; UNCLASSIFIED DRUG;

ACETALIZATION; AMINATION; ARTICLE; AUTOOXIDATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; EPOXIDATION; HYDROGEN BOND; HYDROGENATION; REDUCTION;

EID: 34250713919 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-980349 Document Type: Article

Times cited : (56)

References (30)

1
- 13844294033
- For a review of metal-catalyzed asymmetric reductive amination, see: a
- For a review of metal-catalyzed asymmetric reductive amination, see: (a) Tararov, V. I.; Börner, A. Synlett 2005, 203.
- (2005) Synlett , pp. 203
- Tararov, V.I.¹ Börner, A.²

2
- 28644442668
- For reviews of asymmetric reductions of imines, see:, Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: New York
- (b) For reviews of asymmetric reductions of imines, see: Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis, Suppl. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 2004.
- (2004) Comprehensive Asymmetric Catalysis , Issue.SUPPL. 1
- Ohkuma, T.¹ Noyori, R.²

3
- 0043240879
- (a) Tang, W. J.; Zhang, X. M. Chem. Rev. 2003, 103, 3029.
- (2003) Chem. Rev , vol.103 , pp. 3029
- Tang, W.J.¹ Zhang, X.M.²

4
- 0038260520
- (b) Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
- (2003) Adv. Synth. Catal , vol.345 , pp. 103
- Blaser, H.U.¹ Malan, C.² Pugin, B.³ Spindler, F.⁴ Steiner, H.⁵ Studer, M.⁶

5
- 0037124885
- (c) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2008
- Noyori, R.¹

6
- 33845905749
- (d) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1999.
- (1999) Angew. Chem. Int. Ed , vol.2002 , pp. 41
- Knowles, W.S.¹

7
- 14844293909
- (a) Blaser, H. U.; Pugin, B.; Spindler, F. J. Mol. Catal. A: Chem. 2005, 231, 1.
- (2005) J. Mol. Catal. A: Chem , vol.231 , pp. 1
- Blaser, H.U.¹ Pugin, B.² Spindler, F.³

8
- 0033017113
- (b) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867.
- (1999) Synlett , pp. 867
- Blaser, H.U.¹ Buser, H.P.² Jalett, H.P.³ Pugin, B.⁴ Spindler, F.⁵

9
- 0033522739
- Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2045
- Palmer, M.J.¹ Wills, M.²

10
- 33644935536
- (a) Wang, Z. Y.; Ye, X. X.; Wei, S. Y.; Wu, P. C.; Zhang, A. J.; Sun, J. Org. Lett. 2006, 8, 999.
- (2006) Org. Lett , vol.8 , pp. 999
- Wang, Z.Y.¹ Ye, X.X.² Wei, S.Y.³ Wu, P.C.⁴ Zhang, A.J.⁵ Sun, J.⁶

11
- 33646079612
- (b) Onomura, O.; Kouchi, Y.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 2006, 47, 3751.
- (2006) Tetrahedron Lett , vol.47 , pp. 3751
- Onomura, O.¹ Kouchi, Y.² Iwasaki, F.³ Matsumura, Y.⁴

12
- 28944440055
- (c) Malkov, A. V.; Stoncius, S.; MacDougall, K. N.; Mariani, A.; McGeoch, G. D.; Kocovsky, P. Tetrahedron 2006, 62, 264.
- (2006) Tetrahedron , vol.62 , pp. 264
- Malkov, A.V.¹ Stoncius, S.² MacDougall, K.N.³ Mariani, A.⁴ McGeoch, G.D.⁵ Kocovsky, P.⁶

13
- 0035953044
- (d) Iwasaki, F.; Onomura, O.; Mishima, K.; Kanematsu, T.; Maki, T.; Matsumura, Y. Tetrahedron Lett. 2001, 42, 2525.
- (2001) Tetrahedron Lett , vol.42 , pp. 2525
- Iwasaki, F.¹ Onomura, O.² Mishima, K.³ Kanematsu, T.⁴ Maki, T.⁵ Matsumura, Y.⁶

14
- 30744477746
- (a) 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

15
- 24044465512
- (b) 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

16
- 28044438742
- (c) 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

17
- 25444480017
- (d) 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

18
- 0003590365
- Rappoport, Z, Ed, Wiley: Chichester
- (a) Wittkopp, A.; Schreiner, P. R. In The Chemistry of Dienes and Polymers; Rappoport, Z., Ed.; Wiley: Chichester, 2000.
- (2000) The Chemistry of Dienes and Polymers
- Wittkopp, A.¹ Schreiner, P.R.²

19
- 0037165402
- (b) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
- (2002) Org. Lett , vol.4 , pp. 217
- Schreiner, P.R.¹ Wittkopp, A.²

20
- 0037455338
- (c) Wittkopp, A.; Schreiner, P. R. Chem. Eur. J. 2003, 9, 407.
- (2003) Chem. Eur. J , vol.9 , pp. 407
- Wittkopp, A.¹ Schreiner, P.R.²

21
- 28944449340
- Kotke, M.; Schreiner, P. R. Tetrahedron 2006, 62, 434.
- (2006) Tetrahedron , vol.62 , pp. 434
- Kotke, M.¹ Schreiner, P.R.²

22
- 33750042859
- Kleiner, C. M.; Schreiner, P. R. Chem. Commun. 2006, 4315.
- (2006) Chem. Commun , pp. 4315
- Kleiner, C.M.¹ Schreiner, P.R.²

23
- 0346865819
- For reviews, see: a
- For reviews, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
- (2003) Chem. Soc. Rev , vol.32 , pp. 289
- Schreiner, P.R.¹

24
- 4544221552
- (b) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2062
- Pihko, P.M.¹

25
- 29844448114
- (c) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
- (2005) Org. Biomol. Chem , vol.3 , pp. 4299
- Takemoto, Y.¹

26
- 33646468489
- (d) 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

27
- 33644771025
- Menche, D.; Hassfeld, J.; Li, J.; Menche, G.; Ritter, A.; Rudolph, S. Org. Lett. 2006, 8, 741.
- (2006) Org. Lett , vol.8 , pp. 741
- Menche, D.¹ Hassfeld, J.² Li, J.³ Menche, G.⁴ Ritter, A.⁵ Rudolph, S.⁶

28
- 33645755227
- Menche, D.; Arikan, F. Synlett 2006, 841.
- (2006) Synlett , pp. 841
- Menche, D.¹ Arikan, F.²

29
- 34250754643
- Since it is difficult to avoid the formation of carboxylic acids generated from aldehydes during the reaction, 10 mol% of NaHCO3 was added
- 3 was added.

30
- 34250758831
- General Procedure for the Thiourea-Catalyzed Transfer Hydrogenation of Aldimines In a typical experiment the aldimine 1 (1.0 mmol, thiourea 3 (1 mol, and Hantzsch dihydropyridine 2 (1.1 equiv) were suspended in anhyd CH2Cl2 (5 mL) in a flask. The resulting mixture was allowed to stir at r.t. for 15 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using mixtures of PE and Et2O to afford the pure corresponding amine 4. All compounds were fully characterized on the basis of IR, 1H NMR, 13C NMR and HRMS. Compound 4a: light yellow oil. IR (film, 3418, 1699, 1602, 1505, 1179, 1064 cm-1. 1H NMR (400 MHz, CDCl3, δ, 4.20 (s, 2 H, 6.50-6.52 (d, 2 H, J, 8.71 Hz, 6.59-6.63 (t, 1 H, J, 7.41 Hz, 7.04-7.09 (t, 2 H, J, 7.40 Hz, 7.14-7.27 (m, 5 H, 13C NMR 100 MHz
- 13N: 183.10425; found: 183.10347.

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