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Volumn 45, Issue 4, 2006, Pages 544-547

Enantioselective α-fluorination of carbonyl compounds: Organocatalysis or metal catalysis?

Author keywords

Aldehydes; Asymmetric catalysis; Electrophilic substitution; Fluorination; Organocatalysis

Indexed keywords

ASYMMETRIC CATALYSIS; ELECTROPHILIC SUBSTITUTION; FLUORINATION; ORGANOCATALYSIS;

EID: 31044445377     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502425     Document Type: Review
Times cited : (181)

References (46)
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    • For general overviews of fluorine chemistry, see: a) M. Shimizu, T. Hiyama, Angew. Chem. 2005, 117, 218;
    • (2005) Angew. Chem. , vol.117 , pp. 218
    • Shimizu, M.1    Hiyama, T.2
  • 2
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    • and references therein
    • Angew. Chem. Int. Ed. 2005, 44, 214, and references therein;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 214
  • 5
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    • a) For an important early review on the subject, see: J. T. Welch, Tetrahedron 1987, 43, 3123;
    • (1987) Tetrahedron , vol.43 , pp. 3123
    • Welch, J.T.1
  • 6
    • 4944231418 scopus 로고    scopus 로고
    • Fluorine in the Life Sciences
    • b) Special Issue on "Fluorine in the Life Sciences", ChemBioChem 2004, 5, 557-726.
    • (2004) ChemBioChem , vol.5 , Issue.SPEC. ISSUE , pp. 557-726
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    • reference [1a]
    • For reviews of electrophilic fluorinating agents, see: a) reference [1a];
  • 19
    • 2942702061 scopus 로고    scopus 로고
    • II complexes in enantioselective fluorination has been described in a recent review: H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147;
    • (2004) Chem. Commun. , pp. 1147
    • Ibrahim, H.1    Togni, A.2
  • 20
    • 11144341001 scopus 로고    scopus 로고
    • d) for an informative and up-to-date review on the development of enantioselective fluorination reactions, see: J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119;
    • (2004) Chem. Rev. , vol.104 , pp. 6119
    • Ma, J.-A.1    Cahard, D.2
  • 28
    • 31044433329 scopus 로고    scopus 로고
    • see reference [8d]
    • The cinchona alkaloid mediated enantioselective fluorination can be equally well performed with N-fluoro cinchona alkaloid (Shibata et al.) or with the isolated N-fluoroammonium salts (Cahard et al.) generated in situ. For highly informative discussions, see reference [8d].
  • 35
    • 11144263200 scopus 로고    scopus 로고
    • The higher reactivity of aldehydes over ketones in enamine catalysis has been documented in aldol, α-amination, and α-oxygenation processes: P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
    • (2004) Angew. Chem. , vol.116 , pp. 5248
    • Dalko, P.I.1    Moisan, L.2
  • 37
    • 0001755016 scopus 로고    scopus 로고
    • With the exception of the study by Barbas and co-workers, all α-fluoroaldehydes were immediately reduced to the corresponding α-fluoroalcohols 13 owing to the instability and volatility of the aldehyde products; see: F. A. Davis, P. V. N. Kasu, G. Sundarababu, H. Qi, J. Org. Chem. 1997, 62, 7546.
    • (1997) J. Org. Chem. , vol.62 , pp. 7546
    • Davis, F.A.1    Kasu, P.V.N.2    Sundarababu, G.3    Qi, H.4
  • 43
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    • A direct comparison of metal catalysts and organocatalysts is provided by the recently published studies on the examination of β-ketoesters. The α-amination products can be obtained in up to 90% ee by using cinchona alkaloids as catalysts: a) S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120;
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8120
    • Saaby, S.1    Bella, M.2    Jørgensen, K.A.3
  • 45
    • 0142131252 scopus 로고    scopus 로고
    • II-bisoxazoline complexes afford the α-amination products in outstanding enantioselectivity (up to 99% ee in many cases): c) M. Marigo, K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1405;
    • (2003) Angew. Chem. , vol.115 , pp. 1405
    • Marigo, M.1    Juhl, K.2    Jørgensen, K.A.3
  • 46
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    • Angew. Chem. Int. Ed. 2003, 42, 1367; clearly, other factors such as chemoselectivity, reaction rate, ease of operation, and cost of the catalyst are also issues that need to be taken into account in selecting the asymmetric catalyst.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1367


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.