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Volumn 73, Issue 14, 2008, Pages 5446-5451

Vicarious silylative mukaiyama aldol reaction: A vinylogous extension

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINES; CHEMICAL REACTIONS; KETONES;

EID: 48249106611     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800741c     Document Type: Article
Times cited : (37)

References (40)
  • 7
    • 77957047686 scopus 로고    scopus 로고
    • See also: (g) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Curti, C. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, The Netherlands, 2003; 29 (Bioactive Natural Products (Part J)), pp 449-520.
    • See also: (g) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Curti, C. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, The Netherlands, 2003; Vol. 29 (Bioactive Natural Products (Part J)), pp 449-520.
  • 12
    • 34247161351 scopus 로고    scopus 로고
    • For recent examples of direct Mukaiyama aldol-type reactions triggered by silyl triflate/tertiary amine dual systems see: (a) Downey, C. W, Johnson, M. W. Tetrahedron Lett. 2007, 48, 3559-3562
    • For recent examples of direct Mukaiyama aldol-type reactions triggered by silyl triflate/tertiary amine dual systems see: (a) Downey, C. W.; Johnson, M. W. Tetrahedron Lett. 2007, 48, 3559-3562.
  • 17
    • 34547130040 scopus 로고    scopus 로고
    • Recent reviews on vinylogous aldol and related reactions: a
    • Recent reviews on vinylogous aldol and related reactions: (a) Denmark, S. E.; Heemstra, J. R., Jr J. Org. Chem. 2007, 72, 5668-5688.
    • (2007) J. Org. Chem , vol.72 , pp. 5668-5688
    • Denmark, S.E.1    Heemstra Jr, J.R.2
  • 23
    • 48249096605 scopus 로고    scopus 로고
    • Also, the H-4 proton resonance of syn-isomers is invariably downfield as compared to the corresponding anti-isomeric protons.
    • Also, the H-4 proton resonance of syn-isomers is invariably downfield as compared to the corresponding anti-isomeric protons.
  • 25
    • 48249091526 scopus 로고    scopus 로고
    • Compounds anti-4c and syn-4c are known substances (see ref 7) and provided further confirmation for the relative stereodisposition of their strictly related analogues anti-4a,b and syn-4a,b
    • Compounds anti-4c and syn-4c are known substances (see ref 7) and provided further confirmation for the relative stereodisposition of their strictly related analogues anti-4a,b and syn-4a,b.
  • 26
    • 34247620159 scopus 로고    scopus 로고
    • Actually, one example exists dealing with free tertiary amine-promoted vinylogous aldol addition reactions involving activated furanone and pyrrolinone donors: (a) Sarma, K. D.; Zhang, J.; Curran, T. T. J. Org. Chem. 2007, 72, 3311-3318.
    • Actually, one example exists dealing with free tertiary amine-promoted vinylogous aldol addition reactions involving activated furanone and pyrrolinone donors: (a) Sarma, K. D.; Zhang, J.; Curran, T. T. J. Org. Chem. 2007, 72, 3311-3318.
  • 29
    • 48249113195 scopus 로고    scopus 로고
    • Synthesis of anti-18 and syn-18 congeners has been reported see ref 7
    • Synthesis of anti-18 and syn-18 congeners has been reported (see ref 7).
  • 33
    • 48249153246 scopus 로고    scopus 로고
    • It is known that prolonged exposure of such γ-alkyl-substituted pyrrolinone species to tertiary amine bases in DCM at room temperature results in a thermodynamic equilibration between the 5,1′-syn and 5,1′-anti isomers. See, for example, ref 12b
    • It is known that prolonged exposure of such γ-alkyl-substituted pyrrolinone species to tertiary amine bases in DCM at room temperature results in a thermodynamic equilibration between the 5,1′-syn and 5,1′-anti isomers. See, for example, ref 12b
  • 34
    • 48249119400 scopus 로고    scopus 로고
    • During silica gel flash chromatographic purification, partial desilylation and retrograde aldolization were observed, causing a small erosion of the isolated yield
    • During silica gel flash chromatographic purification, partial desilylation and retrograde aldolization were observed, causing a small erosion of the isolated yield.
  • 37
    • 11844259698 scopus 로고    scopus 로고
    • Mahrwald, R, Ed, Wiley-VCH: Weinheim, Germany
    • (c) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Modern Aldol Reactions
  • 39
    • 48249148058 scopus 로고    scopus 로고
    • With ketone acceptors, the synlanti notation of the ketol products is sometimes ambiguous, depending on the way the formulae are written. For a uniform reading and clean rationalization of the stereochemical results, we opted to positioning the R1 endo-directing group on the plane of the molecule see compounds 5a-c and 23-25 in Tables 1 and 2
    • 1 endo-directing group on the plane of the molecule (see compounds 5a-c and 23-25 in Tables 1 and 2).
  • 40
    • 33747793755 scopus 로고    scopus 로고
    • For a related example involving nucleophilic addition to phenyl ketone 15, see: Roy, S.; Sharma, A.; Chattopadhyay, N.; Chattopadhyay, S. Tetrahedron Lett. 2006, 47, 7067-7069.
    • For a related example involving nucleophilic addition to phenyl ketone 15, see: Roy, S.; Sharma, A.; Chattopadhyay, N.; Chattopadhyay, S. Tetrahedron Lett. 2006, 47, 7067-7069.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.