Chiral-Mn(salen)-complex-catalyzed kinetic resolution of secondary alcohols in water

Angewandte Chemie - International Edition

Volumn 42, Issue 9, 2003, Pages 1042-1044

  Sun, Wei ^a   Wang, Hongwang ^a   Xia, Chungu ^a   Li, Jingwei ^a   Zhao, Peiqing ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Alcohols; Green chemistry; Kinetic resolution; Manganese complexes; Salen ligands

Indexed keywords

ALCOHOLS; COMPLEXATION; MANGANESE; REACTION KINETICS; WATER;

KINETIC RESOLUTION;

CATALYSTS;

ALCOHOL DERIVATIVE; MANGANESE DERIVATIVE; METAL COMPLEX; WATER;

ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; KINETICS; OXIDATION; STEREOCHEMISTRY;

EID: 0037416315     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390268     Document Type: Article

References (48)

1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1993.
2. For a review, see: a) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189;
3. b) T. Katsuki, J. Mol. Catal. A 1996, 113, 87;
4. c) Y. N. Ito, T. Katsuki, Bull. Chem. Soc. Jpn. 1999, 72, 603;
5. d) E. N. Jacobsen, M. H. Hu in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 649;
6. e) T. Katsuki in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 791;
7. f) J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5.
8. a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936;
9. b) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147;
10. c) L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897;
11. d) S. E. Schaus, J. F. Larrow, E. N. Jacobsen, J. Org. Chem. 1997, 62, 4197;
12. e) J. F. Larrow, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420;
13. f) E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773;
14. g) M. Wu, E. N. Jacobsen, J. Org. Chem. 1998, 63, 5252;
15. h) J. A. Miller, W. Jin, S. T. Nguyen, Angew. Chem. 2002, 114, 3077; Angew. Chem. Int. Ed. 2002, 41, 2953.
16. h) J. A. Miller, W. Jin, S. T. Nguyen, Angew. Chem. 2002, 114, 3077; Angew. Chem. Int. Ed. 2002, 41, 2953.
17. W. Sun, H. W. Wang, C. G. Xia, P. Q. Zhao, unpublished results.
18. Catalytic acylation: a) E. Vedejs, J. A. MacKay, Org. Lett. 2001, 3, 535;
19. E. Vedejs, O. Daugulis, J. Am. Chem. Soc. 1999, 121, 5813;
20. E. Vedejs, O. Daugulis, S. T Diver, J. Org. Chem. 1996, 61, 430;
21. S. J. Miller, G. T. Copeland, N. Papaionnou, T. E. Horstmann, E. M. Ruel, J. Am. Chem. Soc. 1998, 120, 1629;
22. J. C. Ruble, H. A. Latham, G. C. Fu, J. Am. Chem. Soc. 1997, 119, 1492;
23. J. C. Ruble, J. Tweddell, G. C. Fu, J. Org. Chem. 1998, 63, 2794;
24. C. E. Garrett, M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 7479;
25. B. Tao, J. C. Ruble, D. A. Hoic, G. C. Fu, J. Am. Chem. Soc. 1999, 121, 5091;
26. T Kawabata, M. Nagato, K. Takasu, K. Fuji, J. Am. Chem. Soc. 1997, 119, 3169;
27. T. Oriyama, Y. Hori, K. Imai, R. Sasaki, Tetrahedron Lett. 1996, 37, 8543;
28. T. Sano, K. Imai, K. Ohashi, T. Oriyama, Chem. Lett. 1999, 265.
29. Enzymatic acylation: a) J. H. Choi, Y. H. Kim, S. H. Nam, S. T. Shin, M.-J. Kim, J. Park, Angew. Chem. 2002, 114, 2479; Angew. Chem. Int. Ed. 2002, 41, 2373;
30. Enzymatic acylation: a) J. H. Choi, Y. H. Kim, S. H. Nam, S. T. Shin, M.-J. Kim, J. Park, Angew. Chem. 2002, 114, 2479; Angew. Chem. Int. Ed. 2002, 41, 2373;
31. b) A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211;
32. b) A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211;
33. c) B. A. Persson, A. L. E. Larsson, M. L. Ray, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 1645;
34. d) B. A. Persson, F. F. Huerta, J.-E. Bäckvall, J. Org. Chem. 1999, 64, 5237;
35. e) F. F. Huerta, J.-E. Bäckvall, Org. Lett. 2001, 3, 1209;
36. f) P. C. D. Jesus, M. C. Rezende, M. D. G. Nascimento, Tetrahedron: Asymmetry 1995, 6, 63.
37. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
38. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
39. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
40. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
41. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
42. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
43. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
44. For the oxidative kinetic resolution of secondary alcohols, see: a) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119; b) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T Katsuki, Tetrahedron 1998, 54, 10017; c) I. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291; d) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288; e) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; f) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475; g) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202.
45. For a recent review, see: a) U. M. Lindström, Chem. Rev. 2002, 102, 2751; b) C. J. Li in Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, (Eds.: P. T. Anastas, T C. Williamson), Oxford, New York, 1998, chap. 14, p. 234.
46. For a recent review, see: a) U. M. Lindström, Chem. Rev. 2002, 102, 2751; b) C. J. Li in Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, (Eds.: P. T. Anastas, T C. Williamson), Oxford, New York, 1998, chap. 14, p. 234.
47. M. Palucki, N. S. Finney, P. J. Pospisil, M. L. Güler, T Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948.
48. rel = ln[(1-C)(1-ee)]/ln[(1-C)(1+ee)], where C is the conversion and ee is the enantiomeric excess; for an excellent discussion of kinetic resolution, see: H. B. Kagan, J. C. Fiaud, Kinetic Resolution, Top. Stereochem. 1988, 18, 249.