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Volumn 9, Issue 22, 2007, Pages 4507-4509

Grignard reagents: Alkoxide-directed iodine-magnesium exchange at sp 3 centers

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EID: 35949004350     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701947y     Document Type: Article
Times cited : (24)

References (35)
  • 1
    • 0003863495 scopus 로고    scopus 로고
    • Richey, H. G, Jr, Ed, Wiley: Chichester
    • (a) Grignard Reagents: New Developments; Richey, H. G., Jr., Ed.; Wiley: Chichester, 2000.
    • (2000) Grignard Reagents: New Developments
  • 2
    • 0003529785 scopus 로고    scopus 로고
    • G. S. Silverman, G. S, Rakita, P. E, Eds, Dekker: New York
    • (b) Handbook of Grignard Reagents; G. S. Silverman, G. S., Rakita, P. E., Eds.; Dekker: New York, 1996.
    • (1996) Handbook of Grignard Reagents
  • 15
    • 0037687811 scopus 로고    scopus 로고
    • For a summary of related functionalized organolithiums, see
    • For a summary of related functionalized organolithiums, see: Najera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867.
    • (2003) Curr. Org. Chem , vol.7 , pp. 867
    • Najera, C.1    Yus, M.2
  • 16
    • 49349138085 scopus 로고
    • For a first report of Mg insertion with pendant magnesium alkoxides, see
    • For a first report of Mg insertion with pendant magnesium alkoxides, see: Cahiez, G.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1978, 3013.
    • (1978) Tetrahedron Lett , pp. 3013
    • Cahiez, G.1    Alexakis, A.2    Normant, J.F.3
  • 24
    • 34250724942 scopus 로고    scopus 로고
    • 2 hybridized organometallics containing hydroxyl or carboxyl functionality: (a) Kopp, F.; Wunderlich, S.; Knochel, P. Chem. Commun. 2007, 2075.
    • 2 hybridized organometallics containing hydroxyl or carboxyl functionality: (a) Kopp, F.; Wunderlich, S.; Knochel, P. Chem. Commun. 2007, 2075.
  • 29
    • 35948985221 scopus 로고    scopus 로고
    • Phenyllithium and MeLi are unable to promote the reaction whereas EtLi and t-BuLi were significantly inferior to the use of BuLi. Employing 2 equiv of ethylhexyllithium, trimethylsilylmethyllithium, or hexyllithium or 1 equiv and an additional equivalent of BuLi and alkylating with cyclohexanone as a test electrophile affords 4a in 34-50% yield.
    • Phenyllithium and MeLi are unable to promote the reaction whereas EtLi and t-BuLi were significantly inferior to the use of BuLi. Employing 2 equiv of ethylhexyllithium, trimethylsilylmethyllithium, or hexyllithium or 1 equiv and an additional equivalent of BuLi and alkylating with cyclohexanone as a test electrophile affords 4a in 34-50% yield.
  • 30
    • 35948978976 scopus 로고    scopus 로고
    • Sequential deprotonation and protonation of 1, 5b, and 5c at -78°C leads to diminishing recovery with 1-iodo-2,2,4-trimethylpentan-3- ol affording only 2-isopropyl-3,3-dimethyloxetane.
    • Sequential deprotonation and protonation of 1, 5b, and 5c at -78°C leads to diminishing recovery with 1-iodo-2,2,4-trimethylpentan-3- ol affording only 2-isopropyl-3,3-dimethyloxetane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.