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Volumn 128, Issue 16, 2006, Pages 5362-5363

Nickel-catalyzed, carbonyl-ene-type reactions: Selective for alpha olefins and more efficient with electron-rich aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE; ALLYL ALCOHOL; BENZYL ALCOHOL; CARBONYL DERIVATIVE; NICKEL; ORGANOPHOSPHORUS COMPOUND; PROPYLENE;

EID: 33646460152     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061471+     Document Type: Article
Times cited : (47)

References (29)
  • 3
    • 0001290261 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (c) Snider, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-561
    • Snider, B.1
  • 13
    • 0008297107 scopus 로고
    • One isolated example of a carbonyl-ene reaction of an aromatic aldehyde and a monosubstituted alkene has been described (yield not reported): Epifani, E.; Florio, S.; Ingrosso, G. Tetrahedron 1988, 44, 5869-5877.
    • (1988) Tetrahedron , vol.44 , pp. 5869-5877
    • Epifani, E.1    Florio, S.2    Ingrosso, G.3
  • 17
    • 0039896797 scopus 로고
    • Lappin, G. R., Sauer, J. D., Eds.; M. Dekker: New York
    • Alpha Olefins Applications Handbook; Lappin, G. R., Sauer, J. D., Eds.; M. Dekker: New York, 1989.
    • (1989) Alpha Olefins Applications Handbook
  • 18
    • 0003106821 scopus 로고    scopus 로고
    • Ni(II)-catalyzed carbonyl-ene reactions of 1,1-disubstituted alkenes and glyoxylate esters: Mikami, K.; Aikawa, K. Org. Lett. 2002, 4, 99-101.
    • (2002) Org. Lett. , vol.4 , pp. 99-101
    • Mikami, K.1    Aikawa, K.2
  • 19
    • 33646460924 scopus 로고    scopus 로고
    • note
    • This selectivity has been observed in one thermal carbonyl-ene reaction (6-methyl-1,5-heptadiene and the highly electron-deficient diethyl oxomalonate, 180 °C, 24 h):
  • 25
    • 33646456927 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 26
    • 33646451827 scopus 로고    scopus 로고
    • note
    • Aldehydes bearing one or more α-hydrogens, e.g., isobutyraldehyde, undergo competitive enolsilane formation.
  • 28
    • 33646438388 scopus 로고    scopus 로고
    • note
    • Reactions of p-nitrobenzaldehyde afforded no trace of coupling product.
  • 29
    • 33646466019 scopus 로고    scopus 로고
    • note
    • Coupling products were not detected when methallylbenzene, cis-4-octene, and trans-4-octene were employed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.