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Volumn 127, Issue 42, 2005, Pages 14817-14824

Origin of enantioselection in chiral alcohol oxidation catalyzed by Pd[(-)-sparteine]Cl2

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; HYDRIDES; HYDROCHLORIC ACID; OXIDATION; PALLADIUM; THERMODYNAMICS;

EID: 27144547160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053195p     Document Type: Article
Times cited : (58)

References (38)
  • 3
    • 4143147456 scopus 로고    scopus 로고
    • Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, Germany
    • For a review on kinetic resolutions of secondary alcohols, see: Somfai, P. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 175-181.
    • (2000) Organic Synthesis Highlights IV , pp. 175-181
    • Somfai, P.1
  • 12
    • 3042699088 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany
    • For a recent review of kinetic resolutions using nucleophilic catalysts, see: Jarvo, E. R.; Miller, S. J. In Comprehensive Asymmetric Catalysis, Supplement; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 2004; pp 189-206.
    • (2004) Comprehensive Asymmetric Catalysis, Supplement , pp. 189-206
    • Jarvo, E.R.1    Miller, S.J.2
  • 16
    • 0035802890 scopus 로고    scopus 로고
    • Kinetic resolution via alcohol oxidation was covered in a review on selective alcohol oxidations, see: Arterburn, J. B. Tetrahedron 2001, 57, 9765-9788.
    • (2001) Tetrahedron , vol.57 , pp. 9765-9788
    • Arterburn, J.B.1
  • 23
    • 0034794864 scopus 로고    scopus 로고
    • (a) A closely related Pd/(-)-sparteine system for aerobic oxidative kinetic resolution was reported simultaneously and independently, see: Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7725-7726
    • Ferreira, E.M.1    Stoltz, B.M.2
  • 24
    • 3142737499 scopus 로고    scopus 로고
    • (b) Also see: Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
    • (2004) Chem. Lett. , vol.33 , pp. 362-367
    • Stoltz, B.M.1
  • 31
    • 27144466621 scopus 로고    scopus 로고
    • note
    • The oxidation rate of (R)-sec-phenethyl alcohol was measured by monitoring the appearance of acetophenone by in situ IR spectroscopy. Oxidation of (S)-sec-phenethyl alcohol was significantly slower, challenging the limitations of that method of monitoring. Instead, the oxidation rate of the (S)-enantiomer was monitored by GC. See Supporting Information for further experimental details.
  • 32
    • 85050296727 scopus 로고
    • Kinetic resolution
    • rel = ln[(1 - C)(1 - ee)]/ln[(1 - C)(1 + ee)], where C is the conversion and ee is the enantiomeric excess, see: Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. Top. Stereochem. 1988, 18, 249-329.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-329
    • Kagan, H.B.1    Fiaud, J.C.2
  • 33
    • 0000868533 scopus 로고
    • Halpern, J. Science 1982, 217, 401-407.
    • (1982) Science , vol.217 , pp. 401-407
    • Halpern, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.