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Volumn 67, Issue 21, 2002, Pages 7238-7243

Uncatalyzed [4 + 2] cycloadditions of 3-nitrocoumarins with vinyl ethers in solventless conditions. A new entry to chromene derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACETALATION; CYCLOADDITIONS;

EID: 0037131237     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0260185     Document Type: Article
Times cited : (61)

References (60)
  • 1
    • 0000180187 scopus 로고
    • and references therein
    • The reaction of α,β-nitroalkenes as 4π components with electronrich olefins is mechanistically distinct involving Michael addition to give betaine followed by collapse to form the nitronate, a formal [4 + 2] adduct: Denmark, S. E.; Dappen, M. S.; Cramer, C. J. J. Am. Chem. Soc. 1986, 108, 1306-1307 and references therein.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1306-1307
    • Denmark, S.E.1    Dappen, M.S.2    Cramer, C.J.3
  • 33
    • 0001352023 scopus 로고    scopus 로고
    • Grieco, P. A., Ed.; Blackie Academic and Professional Publishers: London
    • (c) Fringuelli, F.; Piermatti, O.; Pizzo, F. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional Publishers: London, 1998; pp 223-249 and 250-261.
    • (1998) Organic Synthesis in Water , pp. 223-249
    • Fringuelli, F.1    Piermatti, O.2    Pizzo, F.3
  • 42
    • 2142841449 scopus 로고    scopus 로고
    • note
    • 8c, 12h
  • 43
    • 2142787235 scopus 로고    scopus 로고
    • note
    • 11
  • 45
    • 2142684896 scopus 로고    scopus 로고
    • note
    • The choice of pH is important for the success of the reaction considering the stability of vinyl ethers 8-10 (basic pH) and of 3-nitrocoumarins 5 (acid pH).
  • 57
    • 2142795106 scopus 로고    scopus 로고
    • note
    • The two series of experiments 2, 8, 9 and 11, 16, 17 of Table 2 seem to indicate that the cycloadditions of 5a with 9 and 10 are more diastereoselective when carried out under neat conditions than when they are performed in water.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.