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Volumn 4, Issue 23, 2006, Pages 4281-4284

Organocatalytic regioselective Michael additions of cyclic enones via asymmetric phase transfer catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; DIMERIZATION; DIMERS; ORGANOMETALLICS; PHASE TRANSITIONS; REACTION KINETICS;

EID: 33750986784     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b612606e     Document Type: Article
Times cited : (22)

References (28)
  • 11
    • 47749122232 scopus 로고    scopus 로고
    • Wiley-VCH, Weinheim, Germany, ch. 3 and 4 Differently from 1, chiral non-racemic 2-phenyl cyclohexananones, under solvent free liquid PTC conditions, are diastereoselectively deprotonated on the unexpected 6-position:
    • A. Berkessel and H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, Germany, 2005, ch. 3 and 4
    • (2005) Asymmetric Organocatalysis
    • Berkessel, A.1    Gröger, H.2
  • 21
    • 0037191623 scopus 로고    scopus 로고
    • Recently, Malkov and Koovský reported the benificial effect of a trimethoxy aryl moiety in the organocatalytic allylation of aldehydes; see:
    • S.-S. Jew M.-S. Yoo B.-S. Jeong I. Y. Park H.-g. Park Org. Lett. 2002 4 4245
    • (2002) Org. Lett. , vol.4 , pp. 4245
    • Jew, S.-S.1    Yoo, M.-S.2    Jeong, B.-S.3    Park, I.Y.4    Park, H.-G.5
  • 22
    • 23044461118 scopus 로고    scopus 로고
    • Asymmetric induction in Cinchona alkaloid-mediated PTC stems from weak interactions arising in a thight ion pair; for a useful discussion on the role of the 9-OH see ref. 5c and references cited therein Dendritic Cinchona alkaloids-derived PTC, in which benzyloxy groups substituted on the aromatic moiety in several patterns, have been prepared and employed in the alkylation of benzophenone imine glycine esters:
    • A. V. Malkov M. Bell F. Castelluzzo P. Koovský Org. Lett. 2005 7 3219
    • (2005) Org. Lett. , vol.7 , pp. 3219
    • Malkov, A.V.1    Bell, M.2    Castelluzzo, F.3    Koovský, P.4
  • 24
    • 24344493479 scopus 로고    scopus 로고
    • A similar finding was observed by Jørgensen and co-workers:
    • Q. Zhang D. P. Curran Chem.-Eur. J. 2005 11 4866
    • (2005) Chem.-Eur. J. , vol.11 , pp. 4866
    • Zhang, Q.1    Curran, D.P.2
  • 26
    • 33750986437 scopus 로고
    • The charge delocalization of the 2-cyclopentenone anion can account for the facile isomerization in basic conditions of prostaglandin related systems: see e.g.:
    • H. A. Kaufman and R. P. Napier, German Patent, DE 2016666, 1970, 1105
    • (1970) German Patent, de 2016666 , pp. 1105
    • Kaufman, H.A.1    Napier, R.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.