Bis(oxazolinyl)phenylrhodium(III) Aqua Complex: Efficiency in Enantioselective Addition of Methallyltributyltin to Aldehydes under Aerobic Conditions

Synlett

Volumn , Issue 12, 2003, Pages 1883-1885

  Motoyama, Yukihiro ^a,b   Nishiyama, Hisao ^a,c  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

Aerobic conditions; Allylation; Asymmetric catalysis; Pincer complex; Rhodium

Indexed keywords

ALDEHYDE DERIVATIVE; BIS(OXAZOLINYL)PHENYLRHODIUM; BUTYLTIN DERIVATIVE; METHALLYLTRIBUTYLTIN; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY;

EID: 0142123925     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41474     Document Type: Article

References (34)

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15. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
16. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (1) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
17. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
18. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739.(d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
19. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640.(i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
20. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739.(d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
21. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
22. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
23. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
24. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
25. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
26. For examples of chiral Lewis acid-catalyzed reactions in water-containing solvents, see: (a) Diels-Alder reaction: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975. (b) Also see: Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798. (c) Aldol reaction: Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739. (d) Also see: Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531. (e) Also see: Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165. (f) Also see: Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292. (g) Allylation of aldehydes: Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261. (h) Mannich-type reaction: Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (i) Also see: Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (j) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998. (k) Kobayashi, S. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999, 63. (l) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
27. (a) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375.
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29. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490.
30. Other examples of the recoverable chiral complexes are as follows.: (a) Ru complex for the cyclopropanation: Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223. (b) Ru complex for the oxidation of Sulfides: Schenk, W. A.; Dürr, M. Chem.-Eur. J. 1997, 3, 713. (c) Ru complex for the Diels-Alder reaction: Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem. Int. Ed. 1999, 38, 1220. (d) Ni complex for the 1,3-dipolar cycloaddition: Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
31. Other examples of the recoverable chiral complexes are as follows.: (a) Ru complex for the cyclopropanation: Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223. (b) Ru complex for the oxidation of Sulfides: Schenk, W. A.; Dürr, M. Chem.-Eur. J. 1997, 3, 713. (c) Ru complex for the Diels-Alder reaction: Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem. Int. Ed. 1999, 38, 1220. (d) Ni complex for the 1,3-dipolar cycloaddition: Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
32. Other examples of the recoverable chiral complexes are as follows.: (a) Ru complex for the cyclopropanation: Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223. (b) Ru complex for the oxidation of Sulfides: Schenk, W. A.; Dürr, M. Chem.-Eur. J. 1997, 3, 713. (c) Ru complex for the Diels-Alder reaction: Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem. Int. Ed. 1999, 38, 1220. (d) Ni complex for the 1,3-dipolar cycloaddition: Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
33. Other examples of the recoverable chiral complexes are as follows.: (a) Ru complex for the cyclopropanation: Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223. (b) Ru complex for the oxidation of Sulfides: Schenk, W. A.; Dürr, M. Chem.-Eur. J. 1997, 3, 713. (c) Ru complex for the Diels-Alder reaction: Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem. Int. Ed. 1999, 38, 1220. (d) Ni complex for the 1,3-dipolar cycloaddition: Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
34. Very recently, Portnoy reported the solid-supported Phebox-Rh complexes and its application as heterogeneous catalysts for the allylation of aldehydes, see: Weissberg, A.; Portnoy, M. Chem. Commun. 2003, 1538.