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Volumn 10, Issue 41, 2012, Pages 8260-8267

Organocatalytic dynamic kinetic resolution via conjugate addition: Synthesis of chiral trans-2,5-dialkylcyclohexanones

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CONJUGATE ADDITION; CONJUGATE ADDITION; CYCLOHEXENONES; DIMETHYL MALONATE; DYNAMIC KINETIC RESOLUTION; NOVEL STRATEGIES; ORGANOCATALYTIC;

EID: 84867280564     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob26597d     Document Type: Article
Times cited : (8)

References (38)
  • 29
    • 33645454505 scopus 로고    scopus 로고
    • Enone 6 was selected for optimization of the reaction conditions as masked ketone functionality at the 4th position was visualized as an additional handle for the synthesis of highly substituted cyclohexanone moiety CCDC- contains the supplementary crystallographic data for this paper Computational studies for better understanding of the transition state to justify the observed relative trans stereochemical outcome is planned in future
    • K. R. Knudsen C. E. T. Mitchell S. V. Ley Chem. Commun. 2006 66
    • (2006) Chem. Commun. , pp. 66
    • Knudsen, K.R.1    Mitchell, C.E.T.2    Ley, S.V.3
  • 35
    • 0000328509 scopus 로고
    • At this moment, we are not very sure on the exact role of the base in DKR, however, from the studies mentioned above it is clear that changing base affects diastereoselectivity as well as enantioselectivity. It may be possible that malonate and base forms contact ion pair which participates in the addition reaction affecting diastereoselectivity and enantioselectivity (see
    • V. Gutmann Coord. Chem. Rev. 1976 18 225
    • (1976) Coord. Chem. Rev. , vol.18 , pp. 225
    • Gutmann, V.1
  • 36
    • 4644317493 scopus 로고    scopus 로고
    • It might be due to the conformation of 7-substituted cycloheptenone but at present we are unable to reason this observation We limited our studies to the use of dimethyl and diethyl malonate only, owing to the utility of the Michael addition product.
    • A. J. A. Cobb D. A. Longbottom D. M. Shaw S. V. Ley Chem. Commun. 2004 1808
    • (2004) Chem. Commun. , pp. 1808
    • Cobb, A.J.A.1    Longbottom, D.A.2    Shaw, D.M.3    Ley, S.V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.