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Volumn 27, Issue 19, 2008, Pages 4992-5001

Substrate and catalyst screening in platinum-catalyzed asymmetric alkylation of bis(secondary) phosphines. Synthesis of an enantiomerically-pure C2-symmetric diphosphine

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ALKYLATIONS; BENZYL HALIDES; BORANE ADDUCTS; CATALYST PRECURSORS; CATALYST SCREENINGS; DIASTEREOMERS; DIASTEREOSELECTIVITY; DIPHOSPHINE; EFFICIENT; MODULAR DESIGNS; RECRYSTALLIZATION; SCREENING METHODS; SELECTIVE CATALYSTS; SYNTHESIS OF; X-RAY CRYSTALLOGRAPHIES;

EID: 54249086548     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800534k     Document Type: Article
Times cited : (55)

References (47)
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    • 2a Subsequent duplicate experiments showed that the average diastereoselectivity (dr = 4.2 ±0.3) was reproducibly similar to the first report, while the enantioselectivity (er = 68 ±12 (∼97% ee)) was even higher (Anderson, B. J. Ph.D. Thesis, Dartmouth College, 2008; manuscript in preparation).
    • 2a Subsequent duplicate experiments showed that the average diastereoselectivity (dr = 4.2 ±0.3) was reproducibly similar to the first report, while the enantioselectivity (er = 68 ±12 (∼97% ee)) was even higher (Anderson, B. J. Ph.D. Thesis, Dartmouth College, 2008; manuscript in preparation).
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    • Blaser, H.-U., Schmidt, E., Eds. Asymmetric Catalysis on Industrial Scale. Challenges, Approaches, and Solutions; Wiley-VCH: Weinheim, Germany, 2004. For recent reviews of P-stereogenic phosphines, see:
    • (a) Blaser, H.-U., Schmidt, E., Eds. Asymmetric Catalysis on Industrial Scale. Challenges, Approaches, and Solutions; Wiley-VCH: Weinheim, Germany, 2004. For recent reviews of P-stereogenic phosphines, see:
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    • Some of the results in this article were reported in preliminary form in a patent application: Scriban, C.; Glueck, D. S. WO2007016264, 2007.
    • Some of the results in this article were reported in preliminary form in a patent application: Scriban, C.; Glueck, D. S. WO2007016264, 2007.
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    • 1,2a as a result of the conventions for assigning absolute configuration, (R,R)-Me-DuPhos and (R,R)-i-Pr-DuPhos have opposite configurations. See: Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
    • 1,2a as a result of the conventions for assigning absolute configuration, (R,R)-Me-DuPhos and (R,R)-i-Pr-DuPhos have opposite configurations. See: Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
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    • PC values for these diastereomers were also very similar.
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    • This signal was similar to that reported for analogous AXX' spin systems; see: Redfield, D. A.; Nelson, J. H.; Gary, L. W. Inorg. Nucl. Chem. Lett. 1974, 10, 727-733. The coupling constants were obtained from simulations using gNMR.


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