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Volumn 13, Issue 10, 2011, Pages 2544-2547

Conjugate addition of lithium N -phenyl- N -(α-methylbenzyl)amide: Application to the asymmetric synthesis of (R)-(-)-angustureine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANGUSTUREINE; LITHIUM; MONOUNSATURATED FATTY ACID; ORGANOMETALLIC COMPOUND; QUINOLINE DERIVATIVE;

EID: 79956160271     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200625h     Document Type: Article
Times cited : (52)

References (61)
  • 2
    • 0003573894 scopus 로고
    • Pergamon Press: Oxford,.; March's Advanced Organic Chemistry - Reactions, Mechanisms, and Structure, 5 th ed.; John Wiley & Sons Inc.: New York, 2001.
    • Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992. Smith, M. B.; March, J. March's Advanced Organic Chemistry - Reactions, Mechanisms, and Structure, 5 th ed.; John Wiley & Sons Inc.: New York, 2001.
    • (1992) Conjugate Addition Reactions in Organic Synthesis
    • Perlmutter, P.1    Smith, M.B.2    March, J.3
  • 30
    • 79956085586 scopus 로고    scopus 로고
    • Enantiopure (R)-α-methylbenzylamine (99% ee) is commercially available.
    • Enantiopure (R)-α-methylbenzylamine (99% ee) is commercially available.
  • 32
    • 79956062398 scopus 로고    scopus 로고
    • The enantiomeric purity of (R)- N -phenyl- N -(α-methylbenzyl)amine 1 was determined by chiral HPLC analysis for which the authors would like to thank Darren J. Dixon and Pavol Jakubec.
    • The enantiomeric purity of (R)- N -phenyl- N -(α-methylbenzyl)amine 1 was determined by chiral HPLC analysis for which the authors would like to thank Darren J. Dixon and Pavol Jakubec.
  • 33
    • 79956079008 scopus 로고    scopus 로고
    • The reaction conversion was calculated from the ratio of excess (R)- N -phenyl- N -(α-methylbenzyl)amine 1 to β-amino ester 7 due to the volatility of methyl crotonate 4.
    • The reaction conversion was calculated from the ratio of excess (R)- N -phenyl- N -(α-methylbenzyl)amine 1 to β-amino ester 7 due to the volatility of methyl crotonate 4.
  • 34
    • 79956065495 scopus 로고    scopus 로고
    • An authentic sample of α,β-unsaturated amide 10 was prepared (in 83% yield) via acylation of (R)- N -phenyl- N -(α-methylbenzyl)amine 1 with crotonoyl chloride.
    • An authentic sample of α,β-unsaturated amide 10 was prepared (in 83% yield) via acylation of (R)- N -phenyl- N -(α-methylbenzyl)amine 1 with crotonoyl chloride.
  • 35
    • 79956156640 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 805285.
    • Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 805285.
  • 44
    • 79956133503 scopus 로고    scopus 로고
    • Attempted conjugate addition of lithium (R)- N -phenyl- N -(α-methylbenzyl)amide 2 to 4-methoxyphenyl sorbate [4′- methoxyphenyl (E, E)-hexa-2,4-dieonate] and 4′-methoxyphenyl (E)-4-methylpent-2-enoate under our optimal conditions returned only starting material.
    • Attempted conjugate addition of lithium (R)- N -phenyl- N -(α-methylbenzyl)amide 2 to 4-methoxyphenyl sorbate [4′- methoxyphenyl (E, E)-hexa-2,4-dieonate] and 4′-methoxyphenyl (E)-4-methylpent-2-enoate under our optimal conditions returned only starting material.
  • 45
    • 79956157190 scopus 로고    scopus 로고
    • Unsaturated 4-methoxyphenyl esters 14 - 23 were prepared either by esterification of the corresponding (commercially available) α,β-unsaturated carboxylic acid, or through Wadsworth-Emmons olefination of the corresponding aldehyde using 4-methoxyphenyl diethylphosphonoacetate; see the Supporting Information for full details.
    • α,β-Unsaturated 4-methoxyphenyl esters 14 - 23 were prepared either by esterification of the corresponding (commercially available) α,β-unsaturated carboxylic acid, or through Wadsworth-Emmons olefination of the corresponding aldehyde using 4-methoxyphenyl diethylphosphonoacetate; see the Supporting Information for full details.
  • 47
    • 0043160339 scopus 로고    scopus 로고
    • For previous syntheses of (±)-angustureine, see
    • For previous syntheses of (±)-angustureine, see: Avemaria, F.; Vanderheiden, S.; Braese, S. Tetrahedron 2003, 59, 6785
    • (2003) Tetrahedron , vol.59 , pp. 6785
    • Avemaria, F.1    Vanderheiden, S.2    Braese, S.3
  • 51
    • 70349119910 scopus 로고    scopus 로고
    • For previous syntheses of (S)-(+)-angustureine, see:; Chin. J. Chem. 2004, 22, 932
    • Kothandaraman, P.; Foo, S. J.; Chan, P. W. H. J. Org. Chem. 2009, 74, 5947 For previous syntheses of (S)-(+)-angustureine, see: Lin, X.-F.; Li, Y.; Ma, D.-W. Chin. J. Chem. 2004, 22, 932
    • (2009) J. Org. Chem. , vol.74 , pp. 5947
    • Kothandaraman, P.1    Foo, S.J.2    Chan, P.W.H.3    Lin, X.-F.4    Li, Y.5    Ma, D.-W.6
  • 60
    • 79956160834 scopus 로고    scopus 로고
    • The enantiomeric purity of (R)-(-)-angustureine 36 was determined by chiral HPLC analysis for which the authors would like to thank Darren J. Dixon and Pavol Jakubec.
    • The enantiomeric purity of (R)-(-)-angustureine 36 was determined by chiral HPLC analysis for which the authors would like to thank Darren J. Dixon and Pavol Jakubec.
  • 61
    • 79956098558 scopus 로고    scopus 로고
    • The conditions under which the specific rotation value was recorded (temperature, solvent, concentration) were not reported by Jacquemond-Collet and co-workers in their manuscript describing the isolation of the natural product (see ref 19).
    • The conditions under which the specific rotation value was recorded (temperature, solvent, concentration) were not reported by Jacquemond-Collet and co-workers in their manuscript describing the isolation of the natural product (see ref 19).


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