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Volumn 75, Issue 11, 2010, Pages 3751-3760

Rearrangements and intramolecular diels-alder reactions of normal and vinylogous aza-morita-baylis-hillman products leading to isoindoline derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ARYLIMINES; BORON TRICHLORIDE; CYCLOADDITIONS; CYLOADDITIONS; DIASTEREOMERS; DIASTEREOSELECTIVITIES; DIELS-ALDER; INTRAMOLECULAR DIELS-ALDER REACTION; ISOINDOLINE; METHYL ACRYLATES; MINOR PRODUCTS; PENTADIENYL; POSITIONAL ISOMERS; SUBSTITUTION PATTERNS;

EID: 77952980144     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1005087     Document Type: Article
Times cited : (27)

References (66)
  • 2
    • 11944267498 scopus 로고
    • Jpn. Patent 43003364,; 1968
    • Morita, K. Jpn. Patent 43003364, 1968; Chem Abstr. 1968, 69, 58828s.
    • (1968) Chem Abstr. , vol.69
    • Morita, K.1
  • 12
    • 70249113777 scopus 로고    scopus 로고
    • For lead references, see
    • For lead references, see: Roy, D.; Patel, C.; Sunoj, R. B. J. Org. Chem. 2009, 74, 6936-6943
    • (2009) J. Org. Chem. , vol.74 , pp. 6936-6943
    • Roy, D.1    Patel, C.2    Sunoj, R.B.3
  • 28
    • 0000077082 scopus 로고
    • For the first examples, see
    • For the first examples, see: Perlmutter, P.; Teo, C. C. Tetrahedron Lett. 1984, 25, 5951-5952
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5951-5952
    • Perlmutter, P.1    Teo, C.C.2
  • 64
    • 77952965353 scopus 로고    scopus 로고
    • A small amount of pure 26a was obtained by conducting the reaction with exclusion of oxygen to avoid the formation of 27a
    • A small amount of pure 26a was obtained by conducting the reaction with exclusion of oxygen to avoid the formation of 27a.
  • 65
    • 77952993597 scopus 로고    scopus 로고
    • note
    • The precise role of the Lewis acid in improving the stereoselectivity of formation of 25 relative to 26 is not known. However, when 26b (mixture with 27b) in 1,2-dichloroethane was refluxed in the presence of methylaluminum dichloride, it did not produce any detectable 25b. It is possible that the Lewis acid promotes E, Z isomerization of dienyne 23 prior to the IMDA reaction rather than the epimerization of 26 to 25 after the cycloaddition.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.