Development of a ruthenium-catalyzed asymmetric epoxidation procedure with hydrogen peroxide as the oxidant

Angewandte Chemie - International Edition

Volumn 43, Issue 39, 2004, Pages 5255-5260

  Man, Kin Tse ^a   Döbler, Christian ^a   Bhor, Santosh ^a   Klawonn, Markus ^a   Mägerlein, Wolfgang ^b   Hugl, Herbert ^b   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b BAYER AG   (Germany)

Author keywords

Asymmetric catalysis; Epoxidations; Homogeneous catalysis; Ruthenium

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; EPOXY RESINS; HYDROGEN PEROXIDE; OLEFINS; OXIDATION; SUBSTITUTION REACTIONS;

AROMATIC OLEFINS; EPOXIDATION; PYBOXAZINES;

RUTHENIUM;

ALKENE; AROMATIC COMPOUND; HYDROGEN PEROXIDE; LIGAND; OXIDIZING AGENT; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; EPOXIDATION; SUBSTITUTION REACTION;

EID: 6044260211     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460528     Document Type: Article

References (120)

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5. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
6. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
7. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
8. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
9. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
10. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
11. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
12. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
13. For recent examples see: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346; d) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427; e) Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753; Angew. Chem. Int. Ed. 2001, 40, 3639-3641; f) Y. Nishiyama, T. Hayashi, Y. Nakagawa, N. Mizuno, Stud. Surf. Sci. Catal. 2003, 145, 255-258; g) A. M. Khenkin, L. J. W. Shimon, R. Neumann, Inorg. Chem. 2003, 42, 3331-3339; h) T. Nishimura, S. Uemura, Synlett 2004, 201-216; i) R. Irie, T. Katsuki, Chem. Rec. 2004, 4, 96-109.
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24. For other examples of using oxygen or air, see : a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792; b) I. R. Paeng, K. Nakamoto, J. Am. Chem. Soc. 1990, 112, 3289-3297; c) Metalloporphyrins Catalyzed Oxidations (Eds.: F. Montanari, L. Casella), Kluwer, Dordrecht, 1994; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnant, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661-12662; e) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189; f) K. S. Coleman, C. Y. Lorber, J. A. Osborn, Eur. J. Inorg. Chem. 1998, 1673-1675; g) J. Christoffers, J. Org. Chem. 1999, 64, 7668-7669.
25. For other examples of using oxygen or air, see : a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792; b) I. R. Paeng, K. Nakamoto, J. Am. Chem. Soc. 1990, 112, 3289-3297; c) Metalloporphyrins Catalyzed Oxidations (Eds.: F. Montanari, L. Casella), Kluwer, Dordrecht, 1994; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnant, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661-12662; e) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189; f) K. S. Coleman, C. Y. Lorber, J. A. Osborn, Eur. J. Inorg. Chem. 1998, 1673-1675; g) J. Christoffers, J. Org. Chem. 1999, 64, 7668-7669.
26. For other examples of using oxygen or air, see : a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792; b) I. R. Paeng, K. Nakamoto, J. Am. Chem. Soc. 1990, 112, 3289-3297; c) Metalloporphyrins Catalyzed Oxidations (Eds.: F. Montanari, L. Casella), Kluwer, Dordrecht, 1994; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnant, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661-12662; e) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189; f) K. S. Coleman, C. Y. Lorber, J. A. Osborn, Eur. J. Inorg. Chem. 1998, 1673-1675; g) J. Christoffers, J. Org. Chem. 1999, 64, 7668-7669.
27. For other examples of using oxygen or air, see : a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792; b) I. R. Paeng, K. Nakamoto, J. Am. Chem. Soc. 1990, 112, 3289-3297; c) Metalloporphyrins Catalyzed Oxidations (Eds.: F. Montanari, L. Casella), Kluwer, Dordrecht, 1994; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnant, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661-12662; e) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189; f) K. S. Coleman, C. Y. Lorber, J. A. Osborn, Eur. J. Inorg. Chem. 1998, 1673-1675; g) J. Christoffers, J. Org. Chem. 1999, 64, 7668-7669.
28. For other examples of using oxygen or air, see : a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792; b) I. R. Paeng, K. Nakamoto, J. Am. Chem. Soc. 1990, 112, 3289-3297; c) Metalloporphyrins Catalyzed Oxidations (Eds.: F. Montanari, L. Casella), Kluwer, Dordrecht, 1994; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnant, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661-12662; e) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189; f) K. S. Coleman, C. Y. Lorber, J. A. Osborn, Eur. J. Inorg. Chem. 1998, 1673-1675; g) J. Christoffers, J. Org. Chem. 1999, 64, 7668-7669.
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35. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
36. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
37. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
38. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
39. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
40. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
41. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
42. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
43. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
44. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
45. 2 as oxidant: a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190; b) L. Shu, Y. Shi, J. Org. Chem. 2000, 65, 8807-8810; c) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195 ; d) Y. Shi, J. Synth. Org. Chem. Jpn. 2002, 60, 342-349; e) K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457; f) M. K. Carter, J. Mol. Catal. A 2003, 200, 191-203; g) D. E. De Vos, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2003, 345, 457-473; h) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986; i) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2783-2788; j) G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547-3550; k) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957; l) M. V. Vasylyev, R. Neumann, J. Am. Chem. Soc. 2004, 126, 884-890.
46. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
47. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
48. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
49. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
50. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
51. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
52. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
53. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
54. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
55. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
56. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
57. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
58. 2 see: d) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 3697-3702; e) A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442-3451; f) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642; g) M. Costas, A. K. Tipton, K. Chen, D. H. Jo, L. Que, Jr., J. Am. Chem. Soc. 2001, 123, 6722-6723; h) S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368; i) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150-155; j) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-4657; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
59. Reviews for Ti: a) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 4.1; b) T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1-299.
60. Reviews for Ti: a) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 4.1; b) T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1-299.
61. Reviews for Mn: a) E. N. Jacobsen in Catalytic Asymmetric synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 4.2; b) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 287-325; c) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131-147.
62. Reviews for Mn: a) E. N. Jacobsen in Catalytic Asymmetric synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 4.2; b) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 287-325; c) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131-147.
63. Reviews for Mn: a) E. N. Jacobsen in Catalytic Asymmetric synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 4.2; b) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 287-325; c) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131-147.
64. For examples of asymmetric epoxidation mediated by chiral ketones see: a) D. Yang, Y-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1996, 118, 491-492; b) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806-9807; c) Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224-11235; d) D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1998, 120, 5943-5952, and references therein.
65. For examples of asymmetric epoxidation mediated by chiral ketones see: a) D. Yang, Y-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1996, 118, 491-492; b) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806-9807; c) Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224-11235; d) D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1998, 120, 5943-5952, and references therein.
66. For examples of asymmetric epoxidation mediated by chiral ketones see: a) D. Yang, Y-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1996, 118, 491-492; b) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806-9807; c) Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224-11235; d) D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1998, 120, 5943-5952, and references therein.
67. For examples of asymmetric epoxidation mediated by chiral ketones see: a) D. Yang, Y-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1996, 118, 491-492; b) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806-9807; c) Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224-11235; d) D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, J.-H. Zheng, K.-K. Cheung, J. Am. Chem. Soc. 1998, 120, 5943-5952, and references therein.
68. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
69. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
70. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
71. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
72. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
73. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
74. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
75. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
76. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
77. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
78. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis,
79. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
80. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
81. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
82. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
83. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
84. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
85. 2 as oxidant: a) R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728-734; b) T. Schwenkreis, A. Berkessel, Tetrahedron Lett. 1993, 34, 4785-4788; c) R. Irie, N. Hosoya, T. Katsuki, Synlett 1994, 255-256; d) P. Pietikäinen, Tetrahedron Lett. 1994, 55, 941-944; e) A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, J. Mol. Catal. A 1997, 117, 339-346; f) C. Bolm, D. Kadereit, M. Valacchi, Synlett 1997, 687-688; g) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941; h) R. M. Stoop, A. Mezzetti, Green Chem. 1999, 1, 39-41; i) R. M. Stoop, C. Bauer, P. Setz, M. Wörle, T. Y. H. Wong, A. Mezzetti, Organometallics 1999, 18, 5691-5700; j) R. M. Stoop, S. Bachmann, M. Valentini, A. Mezzetti, Organometallics 2000, 19, 4117-4126; k) C. Bolm, N. Meyer, G. Raabe, T. Weyhermüller, E. Bothe, Chem. Commun. 2000, 2435-2436; l) P. Pietikäinen, J. Mol. Catal. A 2001, 165, 73-79; m) L. Shu, Y. Shi, Tetrahedron 2001, 57, 5213-5218; n) R. I. Kureshy, N.-u. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
86. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
87. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
88. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
89. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
90. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
91. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
92. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
93. For an excellent review using Ru complexes for epoxidation reactions, see: a) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A 1995, 102, 23-39; for achievements in Ru-based epoxidations with different oxidants, see: b) N. End, A. Pfaltz, Chem. Commun. 1998, 589-590; c) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080; d) M. K. Tse, S. Bhor, M. Klawonn, C. Döbler, M. Beller, Tetrahedron Lett. 2003, 44, 7479-7483; e) S. Bhor, M. K. Tse, M. Klawonn, C. Döbler, W. Mägerlein, M. Beller, Adv. Synth. Catal. 2004, 346, 263-267; recent using Ru salen complexes see: f) T. Takeda, R. Irie, Y. Shinoda, T. Katsuki, Synlett 1999, 1157-1159; g) K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki, Chem. Eur. J. 2001, 7, 3776-3782; h) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756.
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114. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].
115. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].
116. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].
117. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].
118. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].
119. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].
120. For examples of catalysis with pybox derivatives, see: a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345; b) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224; c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45; d) G. Sekar, A. Datta-Gupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967; e) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 ; f) C.-X. Zhao, M. O. Duffey, S. J. Taylor, J. P. Morken, Org. Lett. 2001, 3, 1829-1831; g) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; h) D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432, and references in [21a] and [21d].