Synthesis of catalytically active polymers by means of ROMP: An effective approach toward polymeric homogeneously soluble catalysts

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5730-5731

  Bolm, Garsten ^a   Dinter, Christian L ^a   Seger, Andreas ^a   Höcker, Hartwig ^a   Brozio, Jörg ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; POLYMER; ZINC DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ORGANIC CHEMISTRY; POLYMERIZATION; SYNTHESIS;

EID: 0033529729     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990533u     Document Type: Article

References (55)

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28. Optically active bicyclic monoesters can easily be synthesized from meso-anhydrides. For a recent example see: Bolm, C.; Gerlach, A.; Dinter, C. L. Synlett 1999, 195.
29. For the preparation of (R)-4a and its use in dialkylzinc additions to aldehydes, see: (a) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169. (b) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. (c) (S)-4a and its polymer-attached counterparts afforded (S)-configured products.
30. For the preparation of (R)-4a and its use in dialkylzinc additions to aldehydes, see: (a) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169. (b) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. (c) (S)-4a and its polymer-attached counterparts afforded (S)-configured products.
31. For the preparation of (R)-4a and its use in dialkylzinc additions to aldehydes, see: (a) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169. (b) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. (c) (S)-4a and its polymer-attached counterparts afforded (S)-configured products.
32. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
33. (a) Saigo, K.; Usui, M.; Kikuchi, K.; Shimada, E.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1863.
34. (b) Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1979, 18, 707.
35. In this study racemic 8 was used. See also ref 11.
36. (a) Kragl, U.; Dreisbach C.; Wandrey, C. in Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; p 832.
37. (b) Kragl, U.; Dreisbach, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 642.
38. For reviews, see: (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
39. For reviews, see: (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
40. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
41. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
42. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
43. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
44. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
45. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
46. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
47. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
48. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
49. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
50. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
51. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
52. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
53. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
54. Selected polymer-supported ligands for this reaction: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304. (c) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927. (d) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109. (e) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97. (f) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837. (g) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832. (h) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761. (i) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem., Soc. Perkin Trans. 1 1995, 875. (j) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (k) Seebach, D.; Beck, A. K. Chimia 1997, 51, 293. (l) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. (m) Comina, P. J.; Beck, A. K.; Seebach, D. Org. Proc. Res. Dev. 1998, 2, 18. (n) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510. (o) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
55. For a related observation in asymmetric reductions see: Fréchet, J. M. J.; Bald, E.; Lecavalier, P. J. Org. Chem. 1986, 51, 3462.