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Volumn 10, Issue 9, 2008, Pages 1727-1730

Hexafluoroisopropanol as a unique solvent for stereoselective lododesilylation of vinylsilanes

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EID: 58149197555     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800341z     Document Type: Article
Times cited : (91)

References (33)
  • 1
    • 0000395519 scopus 로고    scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: New York, Chapter 3.9, pp
    • Labinger, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York 1996; Vol. 8, Chapter 3.9, pp 667-702.
    • (1996) Comprehensive Organic Synthesis , vol.8 , pp. 667-702
    • Labinger, J.A.1
  • 3
    • 33748586066 scopus 로고    scopus 로고
    • 2nd ed, Schlosser, M, Ed, Wiley: New York, Chapter 8, pp
    • (b) Negishi, E. In Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: New York, 2002; Chapter 8, pp 925-1002.
    • (2002) Organometallics in Synthesis: A Manual , pp. 925-1002
    • Negishi, E.1
  • 6
    • 33748617140 scopus 로고    scopus 로고
    • A practical solution to this problem has been described recently. Huang, Z.; Negishi, E. Org. Lett. 2006, 8, 3675-3678.
    • A practical solution to this problem has been described recently. Huang, Z.; Negishi, E. Org. Lett. 2006, 8, 3675-3678.
  • 7
    • 58149195601 scopus 로고    scopus 로고
    • Useful level of regioselectivity is usually achieved with 2-alkynes. For examples, see ref,3
    • Useful level of regioselectivity is usually achieved with 2-alkynes. For examples, see ref,3
  • 26
    • 85005706466 scopus 로고    scopus 로고
    • Relevant reviews: (a) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786.
    • Relevant reviews: (a) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786.
  • 28
    • 58149190610 scopus 로고    scopus 로고
    • Similar results were obtained by Kishi with electron-rich 2,4-dimethoxy benzoates (ref,14 Table 1C, entry 10-c).
    • (a) Similar results were obtained by Kishi with electron-rich 2,4-dimethoxy benzoates (ref,14 Table 1C, entry 10-c).
  • 29
    • 58149180763 scopus 로고    scopus 로고
    • Relative configuration of the iodohydrin products is based on the anti-addition mechanism and is not confirmed
    • (b) Relative configuration of the iodohydrin products is based on the anti-addition mechanism and is not confirmed.
  • 32
    • 58149195600 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 33
    • 58149192625 scopus 로고    scopus 로고
    • 2, rt, 10 min) provided regioisomeric iodides in 75% combined isolated yield and 1.7:1 ratio, favoring the regioisomer opposite to that obtained from silylcupration-iododesilylation sequence.
    • 2, rt, 10 min) provided regioisomeric iodides in 75% combined isolated yield and 1.7:1 ratio, favoring the regioisomer opposite to that obtained from silylcupration-iododesilylation sequence.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.