Highly enantioselective hydrogenation of simple ketones catalyzed by a Rh-PennPhos complex

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1100-1103

  Jiang, Qiongzhong ^a   Jiang, Yutong ^a   Xiao, Dengming ^a   Cao, Ping ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Chirality; Hydrogenations; Ketones; Rhodium

Indexed keywords

EID: 0032482106     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980504)37:8<1100::aid-anie1100>3.0.co;2-3     Document Type: Article

References (34)

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9. We abbreviate these chiral ligands as PennPhos to indicate that these ligands were made at Penn State University.
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13. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
14. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
15. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
16. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
17. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
18. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
19. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
20. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
21. For oxazaborolidine catalysts, see a) S. Itsuno, K. Ito, A. Hirao, S. Nasahama, J. Chem. Soc. Chem. Commun. 1983, 469; b) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551; for hydrosilylation, see c) H. Brunner, R. Becker, G. Riepl, Organometallics 1984, 3, 1354; d) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500; e) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1994, 106, 92; Angew. Chem. Int. Ed. Engl. 1994, 33, 111; for tranfer hydrogenation, see f) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97; g) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; h) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, ibid. 1995, 117, 7562.
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