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Volumn 9, Issue 18, 2007, Pages 3671-3674

Organocatalytic and highly enantioselective direct α-amination of aromatic ketones

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AROMATIC HYDROCARBON; KETONE; ORGANIC COMPOUND;

EID: 34548537133     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701648x     Document Type: Article
Times cited : (140)

References (74)
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    • For selected reviews on enamine catalysis, see: a
    • For selected reviews on enamine catalysis, see: (a) List, B. Acc. Chem. Res. 2004, 37, 548.
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    • List, B.1
  • 31
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    • 852. For the synthesis of α-amino aryl ketones from chiral α-amino acids, see
    • (d) Li, G.-Q.; Dai, L.-X.; You, S.-L. Chem. Commun. 2007, 852. For the synthesis of α-amino aryl ketones from chiral α-amino acids, see:
    • (2007) Chem. Commun
    • Li, G.-Q.1    Dai, L.-X.2    You, S.-L.3
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    • 33846198424 scopus 로고    scopus 로고
    • For selected examples on enamine catalysis with primary amines, see: a
    • For selected examples on enamine catalysis with primary amines, see: (a) Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2007, 129, 288.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 288
    • Ramasastry, S.S.V.1    Zhang, H.2    Tanaka, F.3    Barbas III, C.F.4
  • 53
    • 34548534874 scopus 로고    scopus 로고
    • Very recently, Kobayashi et al. reported the metal-catalyzed α-amination of aryl ketone derivatives with azodicarboxylates
    • Very recently, Kobayashi et al. reported the metal-catalyzed α-amination of aryl ketone derivatives with azodicarboxylates.
  • 54
    • 33845477661 scopus 로고    scopus 로고
    • Enecarbamates: Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 7993.
    • (a) Enecarbamates: Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 7993.
  • 55
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    • Enesulfonamides: Matsubara, R.; Doko, T.; Uetabe, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 3047.
    • (b) Enesulfonamides: Matsubara, R.; Doko, T.; Uetabe, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 3047.
  • 57
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    • For reviews on cinchona alkaloids as organocatalysts
    • (b) Brunner, H.; Schmidt, P. Eur. J. Org. Chem. 2000, 2119. For reviews on cinchona alkaloids as organocatalysts,
    • (2000) Eur. J. Org. Chem , pp. 2119
    • Brunner, H.1    Schmidt, P.2
  • 60
    • 34548537797 scopus 로고    scopus 로고
    • Using 20 mol, of p-TSA resulted in very low yield < 10
    • Using 20 mol % of p-TSA resulted in very low yield (< 10%).
  • 61
    • 14844316261 scopus 로고    scopus 로고
    • Similar solvent effects have been reported in enamine catalysis, see
    • Similar solvent effects have been reported in enamine catalysis, see: Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 1369
    • Wang, W.1    Wang, J.2    Li, H.3
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    • Dibenzyl azodicarboxylate was also tested, but only a trace amount of the desired α-amination product was isolated due to some side reactions catalyzed by 1e salt
    • Dibenzyl azodicarboxylate was also tested, but only a trace amount of the desired α-amination product was isolated due to some side reactions catalyzed by 1e salt.
  • 63
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    • For reviews, see: (a) Reference 7b.
    • For reviews, see: (a) Reference 7b.
  • 68
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    • Reference 12j. For diamine-protonic acid catalyzed Michael reactions, see:
    • (f) Reference 12j. For diamine-protonic acid catalyzed Michael reactions, see:
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    • Reference 12i
    • (k) Reference 12i.
  • 74
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    • Apart from the promotion of enamine formation, the presence of 4 Å MS may also be helpful for this hydrogen-bonding activation to improve the enantioselectivity.
    • Apart from the promotion of enamine formation, the presence of 4 Å MS may also be helpful for this hydrogen-bonding activation to improve the enantioselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.