Asymmetric Hydrogenation of Ketones with Polymer-Supported Chiral 1,2-Diphenylethylenediamine

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4559-4561

  Li, Xiaoguang ^a   Chen, Weiping ^a   Hems, William ^b   King, Frank ^b   Xiao, Jianliang ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b JOHNSON MATTHEY TECHNOLOGY CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIPHENYLETHYLENEDIAMINE; DIAMINE DERIVATIVE; KETONE; MACROGOL; PHENYL GROUP; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; HYDROGENATION; IMMOBILIZATION; SYNTHESIS;

EID: 0347411082     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0355837     Document Type: Article

References (37)

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18. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
19. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
20. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
21. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
22. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
23. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
24. References for supported BINAP: (a) Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137. (b) ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (c) Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681. (d) Yu, H. B.; Hu, Q. S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (e) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789. (f) Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369. (g) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
25. References for supported DPEN: (a) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257. (b) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015. (c) Bubert, C.; Blacker, J.; Brown, S. M. ; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4037. (d) Chen, Y.-C; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488.
26. References for supported DPEN: (a) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257. (b) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015. (c) Bubert, C.; Blacker, J.; Brown, S. M. ; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4037. (d) Chen, Y.-C; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488.
27. References for supported DPEN: (a) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257. (b) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015. (c) Bubert, C.; Blacker, J.; Brown, S. M. ; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4037. (d) Chen, Y.-C; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488.
28. References for supported DPEN: (a) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257. (b) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015. (c) Bubert, C.; Blacker, J.; Brown, S. M. ; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4037. (d) Chen, Y.-C; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488.
29. While our work was in progress, which was first communicated at the 11th ICI Symposium in May 2002, two publications appeared where DPEN was immobilized through functionalization at the phenyl ring: (a) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825. (b) Ma, Y.-P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J.-G. Org. Lett. 2003, 5, 2103.
30. While our work was in progress, which was first communicated at the 11th ICI Symposium in May 2002, two publications appeared where DPEN was immobilized through functionalization at the phenyl ring: (a) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825. (b) Ma, Y.-P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J.-G. Org. Lett. 2003, 5, 2103.
31. The details of the synthesis will be published elsewhere.
32. PhanePhos: 4,12-bis(diphenylphospino)-[2,2]paracyclophane. See: (a) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173. (b) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P. ; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441.
33. PhanePhos: 4,12-bis(diphenylphospino)-[2,2]paracyclophane. See: (a) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173. (b) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P. ; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441.
34. PhanePhos: 4,12-bis(diphenylphospino)-[2,2]paracyclophane. See: (a) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173. (b) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P. ; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441.
35. The nitrogen content of PEG-2 is 0.61% (or 92% of theoretical loading), which leads to a Ru/7/diamine ratio of 1/1/1.1 in 8.
36. (a) Mikami, K.; Aikawa, K. Org. Lett. 2002, 4, 99.
37. (b) Subongkoj, S.; Lange, S.; Chen, W.; Xiao, J. J. Mol.. Catal. 2003, 196, 125.