Chiral 1,1′-diphosphetanylferrocenes: New ligands for asymmetric catalytic hydrogenation of itaconate derivatives

Angewandte Chemie (International Edition in English)

Volumn 39, Issue 11, 2000, Pages 1981-1984

  Berens, Ulrich ^a   Burk, Mark J ^a   Gerlach, Arne ^a   Hems, William ^a  

^a Chirotech Technology Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78549249036     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (50)

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7. FerroTANE is a trademark of Chirotech Technology Ltd. and is used to refer to the class of ligands of general formula 1,1′-diphosphetanylferrocene.
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40. All substrates of type 7 (including 9) may be prepared readily through Stobbe condensation, followed by cyclic anhydride formation and selective nucleophilic opening of the anhydride with amine nucleophiles; see: a) H. Jendralla, R. Henning, B. Seuring, J. Herchen, B. Kulitzscher, J. Wunner, Synlett 1993, 155;
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42. Available ligands employed in this study: Tol-BINAP = 2,2′-bis(ditolylphosphanyl)-1,1′-binaphthyl; see: R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345. DIPAMP = 1,2-ethanediylbis[(o-methoxyphenyl)-phenylphosphane]; see: B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946. PHANEPHOS = 4,12-bis(diphenylphosphanyl)-[2,2]-paracyclophane; see: P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante, P. J. Reider, J. Am. Chem. Soc. 1997, 119, 6207. BPPM = N-(tertbutoxycarbonyl)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)-methyl] pyrrolidine; see: K. Achiwa, J. Am. Chem. Soc. 1976, 98, 8265.
43. Available ligands employed in this study: Tol-BINAP = 2,2′-bis(ditolylphosphanyl)-1,1′-binaphthyl; see: R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345. DIPAMP = 1,2-ethanediylbis[(o-methoxyphenyl)-phenylphosphane]; see: B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946. PHANEPHOS = 4,12-bis(diphenylphosphanyl)-[2,2]-paracyclophane; see: P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante, P. J. Reider, J. Am. Chem. Soc. 1997, 119, 6207. BPPM = N-(tertbutoxycarbonyl)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)-methyl] pyrrolidine; see: K. Achiwa, J. Am. Chem. Soc. 1976, 98, 8265.
44. Available ligands employed in this study: Tol-BINAP = 2,2′-bis(ditolylphosphanyl)-1,1′-binaphthyl; see: R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345. DIPAMP = 1,2-ethanediylbis[(o-methoxyphenyl)-phenylphosphane]; see: B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946. PHANEPHOS = 4,12-bis(diphenylphosphanyl)-[2,2]-paracyclophane; see: P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante, P. J. Reider, J. Am. Chem. Soc. 1997, 119, 6207. BPPM = N-(tertbutoxycarbonyl)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)-methyl] pyrrolidine; see: K. Achiwa, J. Am. Chem. Soc. 1976, 98, 8265.
45. Available ligands employed in this study: Tol-BINAP = 2,2′-bis(ditolylphosphanyl)-1,1′-binaphthyl; see: R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345. DIPAMP = 1,2-ethanediylbis[(o-methoxyphenyl)-phenylphosphane]; see: B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946. PHANEPHOS = 4,12-bis(diphenylphosphanyl)-[2,2]-paracyclophane; see: P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante, P. J. Reider, J. Am. Chem. Soc. 1997, 119, 6207. BPPM = N-(tertbutoxycarbonyl)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)-methyl] pyrrolidine; see: K. Achiwa, J. Am. Chem. Soc. 1976, 98, 8265.
46. a) M. C. Fournie-Zaluski, A. Coulad, R. Bouboutou, P. Chaillet, J. Devin, G. Waksman, J. Costentin, B. P. Roques, J. Med. Chem. 1985, 28, 1158;
47. b) W. M. Moore, C. A. Spilburg, Biochem. Biophys. Res. Commun. 1986, 136, 390;
48. c) B. Wirz, T. Weisbrod, H. Estermann, Chim. Oggi 1996, 37;
49. d) M. Whittaker, C. D. Floyd, P. Brown, A. J. H. Gearing, Chem. Rev. 1999, 99, 2735.
50. The FerroTANE ligands and rhodium catalysts are available for both research and commercial use through Chirotech Technology Ltd.