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Volumn 44, Issue 10, 2003, Pages 2003-2006

Catalytic asymmetric oxidative lactonizations of meso-diols using a chiral iridium complex

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4,5 (1,2 CYCLOHEXYL) 7 PHOSPHONOHEPTANOIC ACID; ALCOHOL DERIVATIVE; IRIDIUM COMPLEX; LACTONE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PROSTAGLANDIN SYNTHASE INHIBITOR; TRANDOLAPRIL;

EID: 0037416848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00228-4     Document Type: Article
Times cited : (68)

References (32)
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    • for reviews, see: (e) Jones, J. B. Tetrahedron 1986, 42, 3351-3403; (f) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
    • (1986) Tetrahedron , vol.42 , pp. 3351-3403
    • Jones, J.B.1
  • 12
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    • Recently Katsuki developed a chiral salen/Ru catalyst (2 mol%) that promotes aerobic oxidation of meso-diols to give lactols in 59-67% ee in 49-66% yield. See: Shimizu, H.; Nakata, K.; Katsuki, T. Chem. Lett. 2002, 1080-1081 Asymmetric oxidative lactonization of meso-diols using a chiral amino phosphine/Ru catalyst has been reported. See: Ito, M.; Osaku, A.; Ikariya, T. The 84th Annual Meeting of the Chemical Society of Japan, Tokyo, March 2002, Abstr., No. 3 G4-14.
  • 14
    • 0002123299 scopus 로고    scopus 로고
    • For review of asymmetric transfer hydrogenation, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102; (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045-2061.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 97-102
    • Noyori, R.1    Hashiguchi, S.2
  • 15
    • 0033522739 scopus 로고    scopus 로고
    • For review of asymmetric transfer hydrogenation, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102; (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045-2061.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2045-2061
    • Palmer, M.J.1    Wills, M.2
  • 16
    • 34248221331 scopus 로고
    • For other metal-catalyzed desymmetrization of meso-diols, see: (a) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593-1595; (b) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476; (c) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1593-1595
    • Suzuki, T.1    Uozumi, Y.2    Shibasaki, M.3
  • 17
    • 0034823071 scopus 로고    scopus 로고
    • For other metal-catalyzed desymmetrization of meso-diols, see: (a) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593-1595; (b) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476; (c) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7475-7476
    • Jensen, D.R.1    Pugsley, J.S.2    Sigman, M.S.3
  • 18
    • 0034794864 scopus 로고    scopus 로고
    • For other metal-catalyzed desymmetrization of meso-diols, see: (a) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593-1595; (b) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476; (c) 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
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    • note
    • 3), (2S,3R)).
  • 27
    • 85031219345 scopus 로고    scopus 로고
    • The reaction at 0°C gave only 10% yield after 24 h without greatly improving the enantioselectivity (75% ee).
    • The reaction at 0°C gave only 10% yield after 24 h without greatly improving the enantioselectivity (75% ee).
  • 29
    • 85031217943 scopus 로고    scopus 로고
    • The use of other ligands such as (R)-valinol or (1R,2S)-cis-1-amino-2-indanol also gave lower ee with moderate yield
    • The use of other ligands such as (R)-valinol or (1R,2S)-cis-1-amino-2-indanol also gave lower ee with moderate yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.