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Volumn 70, Issue 15, 2005, Pages 5852-5858

Asymmetric synthesis of cyclopropanes from lithiated aryloxiranes and α,β-unsaturated fischer carbene complexes

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; FISCHER-TROPSCH SYNTHESIS; LITHIUM COMPOUNDS; OLEFINS; SUBSTITUTION REACTIONS;

EID: 22244486282     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050443r     Document Type: Article
Times cited : (39)

References (33)
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  • 4
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    • Rappoport, Z., Marek, I., Eds.; John Wiley & Sons: New York, Chapter 18
    • (d) Chemla, F.; Vrancken, E. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; John Wiley & Sons: New York, 2004; Vol. 2, Chapter 18, pp 1165-1242.
    • (2004) The Chemistry of Organolithium Compounds , vol.2 , pp. 1165-1242
    • Chemla, F.1    Vrancken, E.2
  • 5
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    • (e) For a special issue on oxiranyl and aziridinyl anions, see: Florio, S., Ed. Tetrahedron 2003, 59, 9693-9864.
    • (2003) Tetrahedron , vol.59 , pp. 9693-9864
    • Florio, S.1
  • 6
    • 20544436122 scopus 로고    scopus 로고
    • (f) For a recent account on α-lithiated aryloxiranes, see: Capriati, V.; Florio, S.; Luisi, R. Synlett 2005, 9, 1359-1369.
    • (2005) Synlett , vol.9 , pp. 1359-1369
    • Capriati, V.1    Florio, S.2    Luisi, R.3
  • 18
    • 0034301372 scopus 로고    scopus 로고
    • (d) Sierra, M. A. Chem. Rev. 2000, 100, 3591-3638.
    • (2000) Chem. Rev. , vol.100 , pp. 3591-3638
    • Sierra, M.A.1
  • 19
    • 0000887836 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York
    • (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, p 470.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 470
    • Wulff, W.D.1
  • 23
    • 0035296971 scopus 로고    scopus 로고
    • The LUMO of the carbenoid could be, in this case, a strongly polarized σ*c-o orbital. For an exhaustive review on the electrophilic character of carbenoids, see: Boche, G.; Lohrenz, C. W. Chem. Rev. 2001, 101, 697-756.
    • (2001) Chem. Rev. , vol.101 , pp. 697-756
    • Boche, G.1    Lohrenz, C.W.2
  • 24
    • 32744466097 scopus 로고    scopus 로고
    • note
    • A computational and an NMR spectroscopic study on lithiated styrene- and phenylpropylene oxides is underway, and results will be reported in due course.
  • 25
    • 32744458308 scopus 로고    scopus 로고
    • note
    • Crystallographic data for compound 6i have been deposited at the Cambridge Crystallographic Data Centre (deposition no. CCDC-259218). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. [fax: (int.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
  • 29
    • 0004104385 scopus 로고
    • Kagan, H. B., Ed.; Georg Thieme Publishers: Stuttgart
    • The Z or E configuration to diastereomeric enediols 11 could be assigned on the basis of the methine and methyl protons chemical shifts: 5.12 and 1.29 vs 4.31 and 1.03 δ, respectively. In fact, if bulky substituent groups exist on the double bond gem to aromatic rings these will adopt a twist conformation and a shielding of the protons in "cis positions" will occur, as reported (Gaudemar, A. In Stereochemistry: Fundamentals and Methods; Kagan, H. B., Ed.; Georg Thieme Publishers: Stuttgart, 1977;
    • (1977) Stereochemistry: Fundamentals and Methods
    • Gaudemar, A.1
  • 30
    • 32744474438 scopus 로고    scopus 로고
    • Vol. 1. Determination of configurations by spectrometric methods, pp 48-50). A PM3 semiempirical geometry optimization of the Z and E diastereomers showed that the phenyl ring was indeed twisted with respect to the plane of the C=C double bond of about 86° and 73°, respectively, thus supporting the above conclusions.
    • Determination of Configurations by Spectrometric Methods , vol.1 , pp. 48-50
  • 32
    • 0002180970 scopus 로고
    • Organic synthesis via cyclopropanes: Principles and applications
    • Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York; Chapter 8
    • (a) Reissig, H. U. Organic synthesis via cyclopropanes: principles and applications. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 8.
    • (1987) The Chemistry of the Cyclopropyl Group
    • Reissig, H.U.1
  • 33
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    • Biochemistry of the cyclopropyl group
    • Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York; Chapter 16
    • (b) Liu, H. W.; Walsh, C. T. Biochemistry of the cyclopropyl group. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 16.
    • (1987) The Chemistry of the Cyclopropyl Group
    • Liu, H.W.1    Walsh, C.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.