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Volumn 7, Issue 9, 2001, Pages 2015-2027

A new family of chelating diphosphines with a transition metal stereocenter in the backbone: Novel applications of "chiral-at-rhenium" complexes in rhodium-catalyzed enantioselective alkene hydrogenations

Author keywords

Amino acids; Asymmetric hydrogenation; Catalyst; Conformation analysis; Heterobimetallic

Indexed keywords

AMINO ACIDS; BENZENE; CHELATION; CRYSTAL STRUCTURE; METHANOL; OLEFINS; RHODIUM;

EID: 0035805362     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010504)7:9<2015::AID-CHEM2015>3.0.CO;2-H     Document Type: Article
Times cited : (31)

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    • Other literature relevant to points discussed below: a) M. J. Burk, Acc. Chem. Res. 2000, 33, 363; b) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1993, 115, 10125; c) I. D. Gridnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 7183; S. Feldgus, C. R. Landis, J. Am. Chem. Soc. 2000, 122, 12714; e) C. R. Landis, J. Halpern J. Am. Chem. Soc. 1987, 109, 1746;
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    • [34] Typically, the largest group (R″) gives a torsion angle of approximately 180°, such that the X-R″ bond is anti to the Re-C bond. Accordingly, (S)-9 exhibits a Re-C1-P2-C50 torsion angle of - 176.9°; b) for analyses of both conformational and configurational equilibria in related amido and alkoxide complexes, see M. A. Dewey, G. A. Stark, J. A. Gladysz, Organometallics 1996, 15, 4798. At equilibrium, the smallest group (R) prefers the position analogous to the phosphorus lone pair in crystalline (S)-9.
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    • A privately manufactured column was employed, but equal or better separations would be realizable with commercial cyclodextrin fused silica capillary columns (e.g. FS-LIPODEX; Macherey-Nagel)
    • A privately manufactured column was employed, but equal or better separations would be realizable with commercial cyclodextrin fused silica capillary columns (e.g. FS-LIPODEX; Macherey-Nagel).
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