Novel method for efficient aerobic oxidation of silyl ethers to carbonyl compounds catalyzed with N-hydroxyphthalimide (NHPI) and lipophilic Co(II) complexes

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2841-2844

  Karimi, Babak ^a,b   Rajabi, Jamshid ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

^b Institute for Research in Fundamental Sciences   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; CARBONYL DERIVATIVE; COBALT COMPLEX; FUNCTIONAL GROUP; N HYDROXYPHTHALIMIDE; OXYGEN; PHENOL DERIVATIVE; PHTHALIMIDE DERIVATIVE; SILANE DERIVATIVE; TERT BUTYLDIMETHYLSILYLETHYL DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; LIPOPHILICITY; OXIDATION; SENSITIVITY ANALYSIS;

EID: 4444346372     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049294+     Document Type: Article

References (52)

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18. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
19. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
20. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
21. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
22. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
23. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
24. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
25. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
26. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
27. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
28. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
29. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
30. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
31. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
32. Ruthenium catalyst: (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562. (b) Matsumoto, M.; Watanabe, N. J. Org. Chem. 1984, 49, 3435. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (d) Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473. (e) Murahashi, S.-I.; Naota, T.; Hirai, J. J. Org. Chem. 1993, 58, 7318. (f) Wang, G. Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037. (g) Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223. (h) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 1199, 12661. (i) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291. (j) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (k) Kaneda, K.; Ya-mashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1941, 63, 1750. (l) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, M. I.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1941, 63, 7576. Cobalt catalysts: (m) Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 519. (n) Mandal, A. K.; Iqbal, J. Tetrahedron Lett. 1997, 53, 7641. (o) Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502. (p) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
33. Other metals: (q) Semmelhack, M. F.; Schmidt, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374. (r) Coleman, K. S.; Coppe, M.; Thomas, C.; Osborn, J. A. Tetrahedron Lett. 1999, 40, 3723.
34. Other metals: (q) Semmelhack, M. F.; Schmidt, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374. (r) Coleman, K. S.; Coppe, M.; Thomas, C.; Osborn, J. A. Tetrahedron Lett. 1999, 40, 3723.
35. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
36. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
37. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
38. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
39. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
40. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
41. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
42. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
43. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. Chem. Commun. 2002, 3034. (b) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. (d) Ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (f) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538. (g) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 158. (h) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (i) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1941, 63, 3185.
44. (j) For related examples of oxidative kinetic resolutions, see: (k) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725. (l) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835. (m) Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600.
45. (j) For related examples of oxidative kinetic resolutions, see: (k) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725. (l) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835. (m) Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600.
46. (j) For related examples of oxidative kinetic resolutions, see: (k) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725. (l) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835. (m) Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600.
47. For an example of Pd-catalyzed oxidation of alcohols using dichloroethane (DCE), see: (n) Rothenberg, G.; Humbel, S.; Muzart, J. J. Chem. Soc., Perkin Trans. 2 2001, 1998. (o) Muzart, J. Tetrahedron 2003, 59, 5789.
48. For an example of Pd-catalyzed oxidation of alcohols using dichloroethane (DCE), see: (n) Rothenberg, G.; Humbel, S.; Muzart, J. J. Chem. Soc., Perkin Trans. 2 2001, 1998. (o) Muzart, J. Tetrahedron 2003, 59, 5789.
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