Asymmetric Hydrogenation of Ketones with Polymer-Bound BINAP/Diamine Ruthenium Catalysts

Advanced Synthesis and Catalysis

Volumn 343, Issue 4, 2001, Pages 369-375

  Ohkuma, Takeshi ^a   Takeno, Hiroshi ^a   Honda, Yuji ^a   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric hydrogenation; BINAP; Ketone hydrogenation; Polymer bound catalyst

Indexed keywords

EID: 0001352945     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010430)343:4<369::AID-ADSC369>3.0.CO;2-3     Document Type: Article

References (55)

1. (a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, 1994;
2. (b) Comprehensive Asymmetric Catalysis, Vols. 1-3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
3. (c) Catalytic Asymmetric Synthesis, 2nd Ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
4. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
5. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
6. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
7. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
8. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
9. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
10. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
11. Recent reviews: (a) D. Pini, A. Petri, A. Mastantuono, P. Salvadori in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 155-176; (b) S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217-1259; (c) P. Ermert in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 44-84; (d) C. Zumbrunn, T. Masquelin, D. Obrecht in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998, pp. 255-245; (e) B. Pugin, H.-U. Blaser in Comprehensive Asymmetric Catalysis, Vol. 5 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1367-1375; (f) D. E. Bergbreiter in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 45-80; (g) D. J. Bayston, M. E. C. Polywka in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, pp. 211-234; (h) S. Kobayashi, Curr. Opin. Chem. Biol. 2000, 4, 338-345.
12. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
13. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
14. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
15. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
16. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
17. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
18. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
19. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
20. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
21. Recent monographs: (a) Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), Wiley-VCH, Weinheim, 1996; (b) Acc. Chem. Res. (Special Issue on Combinatorial Chemistry) (Eds.: A. W. Czarnik, J. A. Ellman), 1996, 29, 111-170; (c) Chem. Rev. (Special Thematic Issue on Combinatorial Chemistry) (Ed.: J. Szostak), 1997, 97, 347-510; (d) N. K. Terrett, Combinatorial Chemistry, Oxford University Press, Oxford, 1998; (e) B. A. Bunin, The Combinatorial Index, Academic Press, San Diego, 1998; (f) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries (Eds.: D. Obrecht, J. M. Villalgordo), Elsevier, Oxford, 1998; (g) Solid-Phase Organic Synthesis (Ed.: K. Burgess), John Wiley & Sons, New York, 1999; (h) F. Z. Dörwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000; (i) Combinatorial Chemistry (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000; (j) P. Sencci, Solid-Phase Synthesis and Combinatorial Technologies, John Wiley & Sons, New York, 2000.
22. (a) R. Noyori, T. Ohkuma, Pure Appl. Chem. 1999, 71, 1493-1501;
23. (b) R. Noyori, M. Koizumi, D. Ishii, T. Ohkuma, Pure Appl. Chem. 2001, 73, 227-232;
24. (c) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73.
25. (c) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73.
26. (a) R. ter Halle, E. Schulz, M. Spagnol, M. Lemaire, Synlett 2000, 680-682;
27. (b) H.-B. Yu, Q.-S. Hu, L. Pu, Tetrahedron Lett. 2000, 41, 1681-1685;
28. (c) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501. These works utilized different spacers to link the BINAP liagnd and the polymer backbone.
29. D. J. Bayston, J. L. Fraser, M. R. Ashton, A. D. Baxter, M. E. C. Polywka, E. Moses, J. Org. Chem. 1998, 63, 3137-3140.
30. When the reaction was conducted with vigorous stirring, the BINAP-linked polystyrene-beads were gradually broken into powder.
31. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya, R. Noyori, Angew. Chem. 1998, 110, 1792-1796; Angew. Chem. Int. Ed. 1998, 37, 1703-1707.
32. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya, R. Noyori, Angew. Chem. 1998, 110, 1792-1796; Angew. Chem. Int. Ed. 1998, 37, 1703-1707.
33. T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675-2676.
34. 1H NMR.
35. [4] XyIBINAP = 2,2'-bis(di-5,5-xylylphosphino)-1,1′-binaphthyl. DAIPEN= 1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine.
36. [4,8] ToIBINAP = 2,2′-bis(di-4-tolylphosphino)-1,1′-binaphthyl.
37. (a) T. Ohkuma, H. Ooka, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 10417-10418;
38. (b) T. Ohkuma, M. Koizumi, H. Doucet, T. Pham, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1998, 120, 13529-13530.
39. (a) K. Mori, P. Puapoomchareon, Liebigs Ann. Chem. 1991, 1053-1056;
40. (b) K. Mori, Synlett 1995, 1097-1109;
41. (c) R. Croteau, F. Karp in Perfumes: Art, Science and Technology (Eds.: P. M. Müller, D. Lamparsky), Blackie Academic & Professional, London, 1991, pp. 101-126.
42. T. Ohkuma, H. Ikehira, T. Ikariya, R. Noyori, Synlett 1997, 467-468.
43. [15]
44. T. Ohkuma, H. Doucet, T. Pham, K. Mikami, T. Korenaga, M. Terada, R. Noyori, J. Am. Chem. Soc. 1998, 120, 1086-1087.
45. (a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517-519; Angew. Chem. Int. Ed. 1999, 38, 495-497;
46. (a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517-519; Angew. Chem. Int. Ed. 1999, 38, 495-497;
47. (b) K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854-5857; Angew. Chem. Int. Ed. 2000, 39, 3707-3710. Review on Asymmetric Activation:
48. (b) K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854-5857; Angew. Chem. Int. Ed. 2000, 39, 3707-3710. Review on Asymmetric Activation:
49. (c) K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676-3701; Angew. Chem. Int. Ed. 2000, 39, 3532-3556.
50. (c) K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676-3701; Angew. Chem. Int. Ed. 2000, 39, 3532-3556.
51. P. D. Theisen, G. H. Heathcock, J. Org. Chem. 1988, 53, 2374-2378.
52. H. C. Brown, B. T. Cho, W. S. Park, J. Org. Chem. 1988, 53, 1231-1238.
53. H. L. Holland, E. J. Bergen, P. C. Chenchaiah, S. H. Khan, B. Munoz, R. W. Ninniss, D. Richards, Can. J. Chem. 1987, 65, 502-507.
54. T. Shono, N. Kise, E. Shirakawa, H. Matsumoto, E. Okazaki, J. Org. Chem. 1991, 56, 3063-3067.
55. R. Noyori, I. Tomino, M. Yamada, M. Nishizawa, J. Am. Chem. Soc. 1984, 106, 6717-6725.