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Volumn 128, Issue 23, 2006, Pages 7420-7421

Cyanoesterification of 1,2-dienes: Synthesis and transformations of highly functionalized α-cyanomethylacrylate esters

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBOXYLIC ACID DERIVATIVE; 1,2 DIENE DERIVATIVE; 4 AMINOBUTYRIC ACID; ACRYLIC ACID METHYL ESTER; ALKADIENE; ALPHA CYANOMETHYLACRYLATE ESTER DERIVATIVE; BETA AMINO ACID; DICARBOXYLIC ACID; UNCLASSIFIED DRUG;

EID: 33745032031     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0606834     Document Type: Article
Times cited : (93)

References (44)
  • 14
    • 33847803880 scopus 로고
    • Stoichiometric reactions of nickel complexes: (a) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360-2366.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 2360-2366
    • Parshall, G.W.1
  • 39
    • 33745041860 scopus 로고    scopus 로고
    • note
    • Isomers 3 and 4 obtained in this study are readily separable by a single chromatographic separation on silica gel, demonstrating a practical utility of the present reaction.
  • 41
    • 19744369635 scopus 로고    scopus 로고
    • Alternatively, σ-bond methathesis of alkylidene nickelacyclopropane with 1a to give σ-allylnickel 7 followed by isomerization to π-allylnickel 8 and reductive elimination could also account for the formation of 3. (Digram presented). A related mechanism of the nickel-catalyzed reaction of 1,2-dienes, aldehydes, and hydrosilanes, see: Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 7320-7321.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 7320-7321
    • Ng, S.-S.1    Jamison, T.F.2
  • 42
    • 33745039083 scopus 로고    scopus 로고
    • note
    • Although the yield was modest, no detectable amount of regioisomers was obtained, and unlike the case of 3aa, heating the resulting mixture at 100 °C for 24 h after completion of the reaction did not cause the isomerization of 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.