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Volumn 9, Issue 24, 2011, Pages 8253-8260

An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONES; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; GOOD YIELD; MICHAEL REACTIONS; ORGANOCATALYTIC; SYNTHONS; UNSATURATED ALDEHYDES;

EID: 84857572943     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06356a     Document Type: Article
Times cited : (16)

References (57)
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    • D Sole S. García-Rubio L. Vallverdu J. Bonjoch J. Org. Chem. 2001 66 5266
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    • Sole, D.1    García-Rubio, S.2    Vallverdu, L.3    Bonjoch, J.4
  • 18
    • 77955688261 scopus 로고    scopus 로고
    • The potential of the nitrophenyl moiety as a non-conventional activating group for nucleophiles has also been used recently by Melchiorre's group incorporating nitrobenzylpyridines into organocatalytic processes. See
    • M. B. Cid S. Duce S. Morales E. Rodrigo J. L. García Ruano Org. Lett. 2010 12 3586
    • (2010) Org. Lett. , vol.12 , pp. 3586
    • Cid, M.B.1    Duce, S.2    Morales, S.3    Rodrigo, E.4    García Ruano, J.L.5
  • 26
    • 79957985277 scopus 로고    scopus 로고
    • For α-arylation of carbonyl compounds using transition metal catalysis see
    • X. Huang M. Maulide J. Am. Chem. Soc. 2011 133 8510
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 8510
    • Huang, X.1    Maulide, M.2
  • 30
    • 58249115061 scopus 로고    scopus 로고
    • For other methods that do not employ transition metal catalysis see ref. 11c and references cited therein For some organocatalytic examples
    • P. M. Lundin J. Esquivias G. C. Fu Angew. Chem., Int. Ed. 2009 48 154
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 154
    • Lundin, P.M.1    Esquivias, J.2    Fu, G.C.3
  • 36
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    • For details, see Electronic Supplementary Information In order to discard that DBU promoted retro aldol/retro Michael racemizing compounds 4, a sample of alcohols 4g / 4g ′ derived from the Michael addition/aldol reaction of cinnamaldehyde, of known enantiomeric purity, was treated with DBU during 5 h giving rise the same mixture without erosion of ee This phenomenon has been pointed out several times in the literature
    • C. Palomo A. Mielgo Angew. Chem., Int. Ed. 2006 45 7876
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 7876
    • Palomo, C.1    Mielgo, A.2
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    • Gaussian, Inc, Wallingford CT, (see ESI for details and full citation)
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    • (2010) Gaussian 09, Revision B.01
    • Frisch, M.J.1
  • 56
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    • Presumably, torsional effects are again responsible for the observed stereoselectivity. Axial approach of the reagent to C3 is favored as equatorial approach would afford an enolate with a near eclipsing interaction of C3 and C4. See
    • E. Merino R. P. A. Melo M. Ortega-Guerra M. Ribagorda M. C. Carreño J. Org. Chem. 2009 74 2824
    • (2009) J. Org. Chem. , vol.74 , pp. 2824
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.