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Volumn 63, Issue 16, 1998, Pages 5604-5616

Evaluation of Chelation Effects Operative during Diastereoselective Addition of the Allylindium Reagent to 2- And 3-Hydroxycyclohexanones in Aqueous, Organic, and Mixed Solvent Systems

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EID: 0344148449     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980974y     Document Type: Article
Times cited : (59)

References (74)
  • 2
    • 0002446724 scopus 로고
    • Heathcock, C., Ed.; Pergamon Press: Oxford
    • Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.R.1
  • 4
    • 0000677232 scopus 로고
    • (a) Li, C. J. Chem. Rev. 1993, 93, 2023.
    • (1993) Chem. Rev. , vol.93 , pp. 2023
    • Li, C.J.1
  • 5
  • 32
    • 85034464778 scopus 로고    scopus 로고
    • The stereochemical course of this reduction was established on the strength of NOE experiments performed on 13. The key interactions are illustrated here: Formula presented
    • The stereochemical course of this reduction was established on the strength of NOE experiments performed on 13. The key interactions are illustrated here: Formula presented
  • 37
    • 37049058356 scopus 로고
    • The readiness with which axial α-alkyl groups experience epimerization has been previously documented: Cross, B.; Whitham, G. H. J. Chem. Soc. 1961, 1650.
    • (1961) J. Chem. Soc. , pp. 1650
    • Cross, B.1    Whitham, G.H.2
  • 40
    • 85034483817 scopus 로고    scopus 로고
    • The axial disposition of the hydroxyl was clearly evident on the basis of the appearance of the H-2 methine proton as a doublet of doublets (J = 2.6, 2.6 Hz) at δ 3.99. The two small coupling constants arise from neighboring equatorial-equatorial and equatorial-axial spin interactions
    • The axial disposition of the hydroxyl was clearly evident on the basis of the appearance of the H-2 methine proton as a doublet of doublets (J = 2.6, 2.6 Hz) at δ 3.99. The two small coupling constants arise from neighboring equatorial-equatorial and equatorial-axial spin interactions.
  • 43
    • 85034477605 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Kansas, 1993. We thank Professor J. Aubé for making part of this thesis available to us
    • (b) Wang, Y. Ph.D. Thesis, University of Kansas, 1993. We thank Professor J. Aubé for making part of this thesis available to us.
    • Wang, Y.1
  • 47
    • 85034464645 scopus 로고    scopus 로고
    • note
    • 3) ppm 211.9, 68.6, 52.3, 47.8, 38.5, 32.8, 27.7, 21.6.
  • 48
    • 0011877743 scopus 로고
    • (a) Aluminum, magnesium, lithium, potassium, and sodium: Gaudemar, M. Tetrahedron, 1976, 32, 1689.
    • (1976) Tetrahedron , vol.32 , pp. 1689
    • Gaudemar, M.1
  • 59
    • 85034467951 scopus 로고    scopus 로고
    • A diastereoselectivity of >97:3 represents the perceived detection limit of the instrument
    • A diastereoselectivity of >97:3 represents the perceived detection limit of the instrument.
  • 60
    • 0041790137 scopus 로고
    • (a) Bax, A. J. Magn. Reson. 1983, 52, 330; 1983, 53, 517.
    • (1983) J. Magn. Reson. , vol.52 , pp. 330
    • Bax, A.1
  • 61
    • 48749147457 scopus 로고
    • (a) Bax, A. J. Magn. Reson. 1983, 52, 330; 1983, 53, 517.
    • (1983) J. Magn. Reson. , vol.53 , pp. 517
  • 66
    • 85034464602 scopus 로고    scopus 로고
    • Diol 32 was completely unreactive to these conditions
    • Diol 32 was completely unreactive to these conditions.
  • 74
    • 85034466953 scopus 로고    scopus 로고
    • For generic experimental details, see ref 9
    • For generic experimental details, see ref 9,


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.