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Volumn 72, Issue 4, 2007, Pages 1484-1487

Copper-catalyzed multicomponent cascade process for the synthesis of hexahydro-1H-isoindolones

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLOYL CHLORIDES; DIELS-ALDER REACTIONS; DIENYLSTANNANES; IMINES;

EID: 33846956488     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0621773     Document Type: Article
Times cited : (30)

References (26)
  • 4
    • 33846996194 scopus 로고    scopus 로고
    • Sun, S.; Murray, W. V. US 99-12364.5 19990310.
    • Sun, S.; Murray, W. V. US 99-12364.5 19990310.
  • 9
    • 0003397781 scopus 로고    scopus 로고
    • Diederich, F, Stang, P. J, Eds, Wiley-VCH Verlag GmbH: Weinheim
    • Diederich, F., Stang, P. J., Eds. Metal-catalyzed Cross-coupling Reactions; Wiley-VCH Verlag GmbH: Weinheim, 1998.
    • (1998) Metal-catalyzed Cross-coupling Reactions
  • 17
    • 0009508971 scopus 로고
    • For a closely related approach to yohimbine and protoberberine-type alkaloids, see
    • For a closely related approach to yohimbine and protoberberine-type alkaloids, see: Yamaguchi, R.; Hamasaki, T.; Utimoto, K.; Kozima, S.; Takaya, H. Chem. Lett. 1990, 2161.
    • (1990) Chem. Lett , pp. 2161
    • Yamaguchi, R.1    Hamasaki, T.2    Utimoto, K.3    Kozima, S.4    Takaya, H.5
  • 18
    • 33846966878 scopus 로고    scopus 로고
    • Arndtsen reported that the Pd-catalyzed coupling proceeded successfully with m-iodo-substituted aryl imines, see ref 5c
    • Arndtsen reported that the Pd-catalyzed coupling proceeded successfully with m-iodo-substituted aryl imines, see ref 5c.
  • 19
    • 33846952357 scopus 로고    scopus 로고
    • An attempted optimization by variations in the Cu(I) salts, additives Bu4NBr, temperature, and the catalyst loading led only to a minimal improvement
    • 4NBr), temperature, and the catalyst loading led only to a minimal improvement.
  • 21
    • 33846992878 scopus 로고    scopus 로고
    • The relative configuration of the minor diastereomer and the third diastereomer could not be assigned
    • The relative configuration of the minor diastereomer and the third diastereomer could not be assigned.
  • 22
    • 33846960963 scopus 로고    scopus 로고
    • 3,3a are approximately 7.5 Hz. Results of additional NOE experiments are presented in the Supporting Information.
    • 3,3a are approximately 7.5 Hz. Results of additional NOE experiments are presented in the Supporting Information.
  • 24
    • 33846960362 scopus 로고    scopus 로고
    • The presence of additional diastereomers arises likely from the two different configurations at the C-6 position R5, reflecting the presence of E/Z isomers of the diene
    • 5), reflecting the presence of E/Z isomers of the diene.
  • 25
    • 33846947762 scopus 로고    scopus 로고
    • The spectroscopic data available for the minor product 11.2 did not permit a conclusive assignment of the relative stereochemistry.
    • The spectroscopic data available for the minor product 11.2 did not permit a conclusive assignment of the relative stereochemistry.
  • 26
    • 33847006442 scopus 로고    scopus 로고
    • In the major (exo) products 9.1-10 and 12-14 the J3a,7a coupling constants equal approximately 7.0 Hz, and J3,3a coupling constants are in the range of 0-4.5 Hz compare to data in reference 14, In the minor products 9.2-10. the J3a,7a equals approximately 12 Hz, and J3,3a coupling constant are 7 Hz. Notably, the J3,3a coupling constant for isoindolone 11.1 equals 10.6 Hz. Results of additional NOE experiments are presented in the Supporting Information
    • 3,3a coupling constant for isoindolone 11.1 equals 10.6 Hz. Results of additional NOE experiments are presented in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.