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

Angewandte Chemie - International Edition

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

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

^a Chirotech Technology Limited   (United Kingdom)

Author keywords

Asymmetric catalysis; Hydrogenations; P ligands; Peptidomimetics; Rhodium

Indexed keywords

FERROCENE DERIVATIVE; ITACONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HYDROGENATION; OPTICAL ROTATION; REACTION ANALYSIS;

EID: 0034595689     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

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39. 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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41. 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.
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.
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48. The FerroTANE ligands and rhodium catalysts are available for both research and commercial use through Chirotech Technology Ltd.