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Volumn 47, Issue 7, 2008, Pages 2674-2687

Computational study of the factors controlling enantioselectivity in ruthenium(II) hydrogenation catalysts

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; RUTHENIUM DERIVATIVE;

EID: 42449103491     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701981v     Document Type: Article
Times cited : (37)

References (59)
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    • BINAP is 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
    • BINAP is 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
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    • XylBINAP = 2,2′-bis-(di-3,5-xylylphosphino)-1,1′-binaphthyl. DPEN = 1,2-diphenylethylenediamine. (a) Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.
    • XylBINAP = 2,2′-bis-(di-3,5-xylylphosphino)-1,1′-binaphthyl. DPEN = 1,2-diphenylethylenediamine. (a) Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.
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    • TolBINAP = 2,2′-bis(di-4-tolylphosphino)-1,1′-binaphthyl. Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
    • TolBINAP = 2,2′-bis(di-4-tolylphosphino)-1,1′-binaphthyl. Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
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    • 2(R,R-dpen)(R-TolBinap) gave 19% e.e.
    • 2(R,R-dpen)(R-TolBinap) gave 19% e.e.
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    • The source of the van der Walls radii is Bondi, A. J. Phys. Chem. 1964, 68, 441who gives values of 1.20 Å for H, 1.52 Å for O, 1.55 Å for N, and 1.75 Å for C.
    • The source of the van der Walls radii is Bondi, A. J. Phys. Chem. 1964, 68, 441who gives values of 1.20 Å for H, 1.52 Å for O, 1.55 Å for N, and 1.75 Å for C.
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    • Single point calculation at MPWB1K level using the basis sets 6-31+G(d,p) for H, C, N, O, P and LANL2DZ for Ru on the top of PBE/DNP, DSPP optimised geometries. Calculations performed using Gaussian 03 code.
    • (b) Single point calculation at MPWB1K level using the basis sets 6-31+G(d,p) for H, C, N, O, P and LANL2DZ for Ru on the top of PBE/DNP, DSPP optimised geometries. Calculations performed using Gaussian 03 code.
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    • Calculations performed at PBE/DNP level of theory for the hydrogen transfer acetone/i-propyl alcohol reaction catalysed by model trans-Ru(H)2(diphosphine)(diamine) catalysts. The structure of the optimized transition states can be found in Table 5
    • 2(diphosphine)(diamine) catalysts. The structure of the optimized transition states can be found in Table 5.
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    • Correlation based on low temperature neutron diffraction data. Steiner. T.; Majerz, I.; Wilson, C. C. Angew. Chem., Int. Ed. 2001, 40, 2651.


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