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Volumn 20, Issue 22, 2001, Pages 4607-4615

Catalytic and photochemical cyclopropanation of alkenes with methyl diazo(trialkylsilyl)acetates: Steric effects and thermodynamic stabilities of cyclopropanes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANES; DIAZO ESTERS; METHYL DIAZOTRIALKYLSILYLACETATES; PHOTOCHEMICAL CYCLOPROPANATION; STERIC EFFECTS;

EID: 0035969296     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010491b     Document Type: Article
Times cited : (19)

References (69)
  • 24
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    • note; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, Germany; Workbench Edition E21; (Stereoselective Synthesis)
    • (a) For recent reviews on simple diastereoselectivity in cyclopropanation reactions with acylcarbenes, see: (a) Reissig, H.-U. In Methods of Organic Chemistry, Houben-Weyl; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, Germany, 1996; Workbench Edition E21, Vol. 5 (Stereoselective Synthesis), pp 3220-3226.
    • (1996) Methods of Organic Chemistry, Houben-Weyl , vol.5 , pp. 3220-3226
    • Reissig, H.-U.1
  • 25
    • 0001653975 scopus 로고    scopus 로고
    • de Meijere, A., Eds.; Thieme: Stuttgart, Germany; (Carbocyclic Three-Membered Ring Compounds)
    • (b) Maas, G. In Methods of Organic Chemistry, Houben-Weyl; de Meijere, A., Eds.; Thieme: Stuttgart, Germany, 1997; Vol E17a (Carbocyclic Three-Membered Ring Compounds), pp 405-515.
    • (1997) Methods of Organic Chemistry, Houben-Weyl , vol.E17a , pp. 405-515
    • Maas, G.1
  • 41
    • 0002699922 scopus 로고
    • note
    • It should be recalled that dinuclear rhodium carboxylates have only one open coordination site per metal atom, while copper(I) has two; this difference may also lead to a different cyclopropanation mechanism in the copper case: (a) Doyle, M. P.; Griffin, J. H.; Bagheri, V.; Dorow, R. L. Organometallics 1984, 3, 53.
    • (1984) Organometallics , vol.3 , pp. 53
    • Doyle, M.P.1    Griffin, J.H.2    Bagheri, V.3    Dorow, R.L.4
  • 46
    • 0011427951 scopus 로고
    • Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York
    • (b) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2, p 59.
    • (1981) Reactive Intermediates , vol.2 , pp. 59
    • Moss, R.A.1    Jones M., Jr.2
  • 54
    • 0000166261 scopus 로고
    • note
    • The fluoride-induced desilylation of methyl 1-(trimethylsilyl)-cyclopropanecarboxylate is known; however, this example has no stereochemical implication: Paquette, L. A.; Blankenship, C.; Wells, G. J. J. Am. Chem. Soc. 1984, 106, 6442.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6442
    • Paquette, L.A.1    Blankenship, C.2    Wells, G.J.3
  • 62
    • 0011419807 scopus 로고    scopus 로고
    • note
    • (a) MM2 calculations were carried out using the software package PCMODEL, which is a PC version of the MMX package, developed by Serena Software, P.O. Box 3076, Bloomington, IN 47402-3076.
  • 63
    • 84986437005 scopus 로고
    • MacroModel V3.5X
    • note
    • (b) MM2* calculations were carried out using the software package MacroModel: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel V3.5X. J. Comput. Chem. 1990, 11, 440. The MM2* force field treats electrostatics and conjugation differently than the original MM2 force field. Further information can be obtained from the user's manual of MacroModel.
    • (1990) J. Comput. Chem. , vol.11 , pp. 440
    • Mohamadi, F.1    Richards, N.G.J.2    Guida, W.C.3    Liskamp, R.4    Caufield, C.5    Chang, G.6    Hendrickson, T.7    Still, W.C.8
  • 64
    • 0024821263 scopus 로고
    • (c) Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551, 8566, 8576. The MM3(96) package is available from Tripos, Inc., 1699 South Hanley Road, Suite 303, St. Louis, MO 63144.
    • (1989) J. Am. Chem. Soc. , vol.111
    • Allinger, N.L.1    Yuh, Y.H.2    Lii, J.-H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.