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Volumn 54, Issue 35, 1998, Pages 10389-10402

Asymmetric aldol additions catalyzed by chiral phosphoramides: Electronic effects of the aldehyde component

Author keywords

[No Author keywords available]

Indexed keywords

2 [HYDROXY (3,4,5 TRIMETHOXYPHENYL)METHYL]CYCLOHEPTANONE; 2 [HYDROXY (4 METHOXYPHENYL)METHYL]CYCLOHEPTANONE; 2 [HYDROXY [3,5 BIS(TRIFLUOROMETHYL)PHENYL]METHYL]CYCLOHEPTANONE; 2 [HYDROXY [4 (TRIFLUOROMETHYL)PHENYL]METHYL]CYCLOHEPTANONE; 2 [HYDROXY(PHENYL)METHYL]CYCLOHEPTANONE; 2 [HYDROXY(PHENYL)METHYL]CYCLOPENTANONE; ALDEHYDE; CYCLOHEPTANONE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; KETONE; MERCURY; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032572895     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00493-1     Document Type: Article
Times cited : (52)

References (35)
  • 1
    • 33748238772 scopus 로고
    • (1) For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 417
    • Bach, T.1
  • 6
    • 0000312386 scopus 로고    scopus 로고
    • Edition E21; Helmchen, G.; Hoffman, R.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart
    • (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
    • (1996) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl) , vol.3 , pp. 1730-1736
    • Braun, M.1
  • 15
    • 0030827816 scopus 로고    scopus 로고
    • (5) Recently Yamamoto has described a silver(I)-catalyzed aldol addition of stannyl enolates to aldehydes which also correlates starting enolate geometry and the major diastereomer: Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9319
    • Yanagisawa, A.1    Matsumoto, Y.2    Nakashima, H.3    Asakawa, K.4    Yamamoto, H.5
  • 19
    • 0000982492 scopus 로고
    • (8) For a review of the conversion of TMS enol ethers to reactive enolates see: Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181.
    • (1985) Acc. Chem. Res. , vol.18 , pp. 181
    • Kuwajima, I.1    Nakamura, E.2
  • 21
    • 0010442589 scopus 로고    scopus 로고
    • note
    • (10) The relative configuration was established on the basis of the splitting pattern and resonance frequency of the hydroxyl bearing methine. The proton appears as a broad singlet in the syn-isomer and as a doublet or doublet of doublets in the anti-isomer. In addition, this proton in the anti-isomer appears 0.4-0.7 ppm upfield of the syn-isomer.
  • 23
    • 0010518375 scopus 로고    scopus 로고
    • See also ref. 4b
    • (b) See also ref. 4b.
  • 32
    • 0001924338 scopus 로고
    • Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Wiley Interscience: New York, See also refs. 8 and 16
    • (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. in Topics in Stereochemistry; Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Wiley Interscience: New York, 1982; Vol. 13, p1. See also refs. 8 and 16.
    • (1982) Topics in Stereochemistry , vol.13 , pp. 1
    • Evans, D.A.1    Nelson, J.V.2    Taber, T.R.3
  • 33
    • 0010445805 scopus 로고    scopus 로고
    • note
    • (17) The absolute configuration of the (-)-anti-5c was determined to be (2R,1′S) by X-ray crystallographic analysis of the corresponding 4-bromobenzoate. The absolute configurations of the other anti diastereomers are assigned by analogy. The absolute configurations of the syn diastereomers were not established.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.