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Volumn 9, Issue 10, 2007, Pages 1911-1914

Computational study of the stereochemistry of intramolecular carbolithiation of an alkene by a secondary alkyllithium: Stereochemistry change caused by a single THF molecule of solvation

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EID: 34249303403     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070453     Document Type: Article
Times cited : (17)

References (30)
  • 1
    • 34249297449 scopus 로고    scopus 로고
    • Reviews: Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; 3, pp 251-273. Mealy, M. J.; Bailey, W. F. J. Organomet. Chem. 2002, 646, 59-67.
    • (a) Reviews: Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. Mealy, M. J.; Bailey, W. F. J. Organomet. Chem. 2002, 646, 59-67.
  • 3
    • 14844321307 scopus 로고    scopus 로고
    • Recent papers: Bailey, W. F.; Jiang, X. L. Tetrahedron 2005, 61, 3183-3194.
    • (b) Recent papers: Bailey, W. F.; Jiang, X. L. Tetrahedron 2005, 61, 3183-3194.
  • 9
    • 34249278171 scopus 로고    scopus 로고
    • The corresponding carbometallations with Mg and Na, occurring at higher temperatures, also produce mainly trans products
    • The corresponding carbometallations with Mg and Na, occurring at higher temperatures, also produce mainly trans products.
  • 10
    • 49649150095 scopus 로고    scopus 로고
    • Mg: Kossa, J. W. C.; Rees, T. C.; Richey, J. H. G. Tetrahedron Lett. 1971, 12, 3455-3458.
    • (a) Mg: Kossa, J. W. C.; Rees, T. C.; Richey, J. H. G. Tetrahedron Lett. 1971, 12, 3455-3458.
  • 11
    • 0010371693 scopus 로고    scopus 로고
    • Na: Garst, G. F.; Hines, Jr., J. B. J. Am. Chem. Soc. 1984, 106, 6443-6445. Garst, G. F.; Hines, Jr., J. B.; Bruhnke, J. D. Tetrahedron Lett. 1986, 27, 1963-1966.
    • (b) Na: Garst, G. F.; Hines, Jr., J. B. J. Am. Chem. Soc. 1984, 106, 6443-6445. Garst, G. F.; Hines, Jr., J. B.; Bruhnke, J. D. Tetrahedron Lett. 1986, 27, 1963-1966.
  • 13
    • 0141706619 scopus 로고    scopus 로고
    • Yus et al. have performed the cyclization of the analogue of 2 in which a n-propyl group replaces the methyl group and obtained a single diastereomer the configuration of which was not determined. However, based on an analysis using the molecular model of Bailey et al.,3 they suggested that the product was most likely cis: Yus, M.; Ortiz, R.; Huerta, F. F. Tetrahedron 2003, 59, 8525-8542.
    • Yus et al. have performed the cyclization of the analogue of 2 in which a n-propyl group replaces the methyl group and obtained a single diastereomer the configuration of which was not determined. However, based on an analysis using the molecular model of Bailey et al.,3 they suggested that the product was most likely cis: Yus, M.; Ortiz, R.; Huerta, F. F. Tetrahedron 2003, 59, 8525-8542.
  • 27
    • 34249319168 scopus 로고    scopus 로고
    • Frisch, M. J. et al. Gaussian 03, Revision C.01; Gaussian, Inc.: Wallingford CT, 2004. Full reference provided in Supporting Information.
    • Frisch, M. J. et al. Gaussian 03, Revision C.01; Gaussian, Inc.: Wallingford CT, 2004. Full reference provided in Supporting Information.
  • 30
    • 0003998388 scopus 로고    scopus 로고
    • 85th ed, Lide, D. R, Ed, CRC Press: Boca Raton, Chapter 5
    • CRC Handbook of Chemistry and Physics, 85th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, 2004; Chapter 5.
    • (2004) CRC Handbook of Chemistry and Physics


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.