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Volumn 50, Issue 32, 2009, Pages 4602-4605

Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; ETHER DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE;

EID: 67449088256     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.065     Document Type: Article
Times cited : (53)

References (49)
  • 1
    • 0032512595 scopus 로고    scopus 로고
    • For recent reviews on enantioselective aldol reaction, see:
    • For recent reviews on enantioselective aldol reaction, see:. Nelson S.G. Tetrahedron: Asymmetry 9 (1998) 357-389
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 357-389
    • Nelson, S.G.1
  • 6
    • 0036105811 scopus 로고    scopus 로고
    • For reviews on direct aldol reaction, see:
    • For reviews on direct aldol reaction, see:. Alcaide B., and Almendros P. Eur. J. Org. Chem. (2002) 1595-1601
    • (2002) Eur. J. Org. Chem. , pp. 1595-1601
    • Alcaide, B.1    Almendros, P.2
  • 12
    • 0034614028 scopus 로고    scopus 로고
    • For related catalyses, see:
    • For related catalyses, see:. Trost B.M., and Ito H. J. Am. Chem. Soc. 122 (2000) 12003-12004
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12003-12004
    • Trost, B.M.1    Ito, H.2
  • 20
    • 0037011290 scopus 로고    scopus 로고
    • Although the substrates are limited to glycine Schiff bases, the aldol reactions promoted by phase transfer catalysts have been reported, see:
    • Although the substrates are limited to glycine Schiff bases, the aldol reactions promoted by phase transfer catalysts have been reported, see:. Ooi T., Taniguchi M., Kameda M., and Maruoka K. Angew. Chem., Int. Ed. 41 (2002) 4542-4544
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4542-4544
    • Ooi, T.1    Taniguchi, M.2    Kameda, M.3    Maruoka, K.4
  • 25
    • 6044269452 scopus 로고    scopus 로고
    • For recent reviews on related organocatalyses, see:
    • For recent reviews on related organocatalyses, see:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed 43 (2004) 5138-5175
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 5138-5175
    • Dalko, P.I.1    Moisan, L.2
  • 36
    • 67449106605 scopus 로고    scopus 로고
    • note
    • Although adding tetrachlorosilane to the mixture of the other components gave the same results, adding a ketone to the mixture decreased the stereoselectivities.
  • 38
    • 67449093803 scopus 로고    scopus 로고
    • note
    • The signal of the olefin proton was observed at 5.28 ppm derived from cyclohexanone. See Supplementary data.
  • 39
    • 1842782790 scopus 로고    scopus 로고
    • Denmark reported that HMPA catalyzed the formation of the trichlorosilyl enol ether of isobutyraldehyde with tetrachlorosilane and 2,4,6-trimethylpyridine, see:
    • Denmark reported that HMPA catalyzed the formation of the trichlorosilyl enol ether of isobutyraldehyde with tetrachlorosilane and 2,4,6-trimethylpyridine, see:. Denmark S.E., and Bui T. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5439-5444
    • (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 5439-5444
    • Denmark, S.E.1    Bui, T.2
  • 40
    • 0035905368 scopus 로고    scopus 로고
    • For recent reports on asymmetric cross-aldol reactions of aldehyde enolate equivalents, see:
    • For recent reports on asymmetric cross-aldol reactions of aldehyde enolate equivalents, see:. Denmark S.E., and Ghosh S.K. Angew. Chem., Int. Ed. 40 (2001) 4759-4762
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4759-4762
    • Denmark, S.E.1    Ghosh, S.K.2
  • 46
    • 67449083739 scopus 로고    scopus 로고
    • note
    • (R)-3,3′-Dimethyl-2,2′-biquinoline N,N′-dioxide catalyzed the reaction of benzaldehyde and isobutyraldehyde with a similar stereoselectivity but with lower chemical yield (2 h, 71%, 55% ee).
  • 47
    • 0032473509 scopus 로고    scopus 로고
    • For a review on enantioselective construction of quaternary carbon centers, see:
    • For a review on enantioselective construction of quaternary carbon centers, see:. Corey E.J., and Guzman-Perez A. Angew, Chem., Int. Ed. 37 (1998) 388-401
    • (1998) Angew, Chem., Int. Ed. , vol.37 , pp. 388-401
    • Corey, E.J.1    Guzman-Perez, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.