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Volumn 49, Issue 26, 2008, Pages 4089-4091

Olefin exchange-mediated cyclopropanation of nitriles with homoallylic alcohols

Author keywords

Aminocyclopropane; Cyclopropanation; Homoallylic alcohols; Nitrile; Titanium

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; NITRILE;

EID: 43849109354     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.133     Document Type: Article
Times cited : (10)

References (39)
  • 21
    • 43849097242 scopus 로고    scopus 로고
    • Lee, J.; Lee, J. C.; Cha, J. K., unpublished results.
    • Lee, J.; Lee, J. C.; Cha, J. K., unpublished results.
  • 31
    • 0000458209 scopus 로고
    • For a review on substrate-directed reactions, see:
    • For a review on substrate-directed reactions, see:. Hoveyda A.H., Evans D.A., and Fu G.C. Chem. Rev. 93 (1993) 1307
    • (1993) Chem. Rev. , vol.93 , pp. 1307
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 32
    • 43849112958 scopus 로고    scopus 로고
    • note
    • The cyclopentyl Grignard reagent was not used in these experiments, as it was known to react with nitriles in the presence of titanium isopropoxides to give the respective bicyclic aminocyclopropanes (Ref. 3d).
  • 33
    • 0011843549 scopus 로고    scopus 로고
    • For other examples on significant differences in the reactivity between cyclopentyl and cyclohexyl Grignard reagents, see:
    • For other examples on significant differences in the reactivity between cyclopentyl and cyclohexyl Grignard reagents, see:. Quan L.G., and Cha J.K. Org. Lett. 3 (2001) 2745
    • (2001) Org. Lett. , vol.3 , pp. 2745
    • Quan, L.G.1    Cha, J.K.2
  • 34
    • 43849112957 scopus 로고    scopus 로고
    • See also Ref. 7c.
    • See also Ref. 7c.
  • 37
    • 43849101855 scopus 로고    scopus 로고
    • note
    • TMSCl was also utilized successfully, but the resulting reactions were slightly less clean than those with TMSOTf.
  • 38
    • 43849109359 scopus 로고    scopus 로고
    • note
    • 4OH 50:1:0→10:1:0.04) to afford hydroxypyran 4e (20 mg, 28%) and aminocyclopropane 3e (47 mg, 67%).
  • 39
    • 43849104655 scopus 로고    scopus 로고
    • Kim, K.; Cha, J. K., unpublished results.
    • Kim, K.; Cha, J. K., unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.