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Volumn 131, Issue 38, 2009, Pages 13819-13825

Organocatalytic synthesis of spiro[pyrrolidin-3,3′-oxindoles] with high enantiopurity and structural diversity

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; AZOMETHINE YLIDES; BIOLOGICAL ACTIVITIES; DIPOLAR CYCLOADDITIONS; DIVERSITY-ORIENTED SYNTHESIS; ENANTIO; ENANTIOPURITY; ENANTIOSELECTIVE; HIGH YIELD; INDOLE RINGS; MEDICINAL CHEMISTRY; ORGANOCATALYTIC; OXINDOLES; RAPID SYNTHESIS; REGIOCHEMISTRY; STACKING INTERACTION; STRUCTURAL DIVERSITY; THEORETICAL CALCULATIONS; THREE-COMPONENT;

EID: 70349742473     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905302f     Document Type: Article
Times cited : (550)

References (33)
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    • Catalytic synthesis of spiro[pyrrolidin-3,3′-oxindoles] includes asymmetric intramolecular Heck reaction; see
    • (a) Catalytic synthesis of spiro[pyrrolidin-3,3′-oxindoles] includes asymmetric intramolecular Heck reaction; see: Overman, L. E.; Rosen, M. D. Angew. Chem., Int. Ed. 2000, 39, 4596.
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    • For very recent organocatalytic conjugate additions of oxindoles to electronically poor olefins for the generation of all-carbon quaternary stereogenic center, see: (c)
    • For very recent organocatalytic conjugate additions of oxindoles to electronically poor olefins for the generation of all-carbon quaternary stereogenic center, see: (c) Bui, T.; Syed, S.; Barbas, C. F. J. Am. Chem. Soc. 2009, 131, 8758.
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    • For an excellent review on the importance of diversity-oriented organic synthesis in drug discovery, see: Schreiber, S. L. Science 2000, 287, 1964.
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    • For discussion on regioselectivity of 1,3-dipolar addition reactions, see: (a) and refs 16a, 16b
    • For discussion on regioselectivity of 1,3-dipolar addition reactions, see: (a) Houk, K. N.; Sims, J.; Watts, C. R.; Luskus, L. J. J. Am. Chem. Soc. 1973, 95, 7301, and refs 16a, 16b.
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    • note
    • All calculations were performed with the Gaussian 03 program.
  • 30
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    • The aromatic stacking interaction between the aryl groups to fix the geometry in chiral phosphoric acid catalysis; see
    • (c) The aromatic stacking interaction between the aryl groups to fix the geometry in chiral phosphoric acid catalysis; see: Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2007, 129, 6756.
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    • The proposed zwitterionic resonance forms are similar to the principal resonance forms of the carbanion intermediate in transamination reactions; see
    • (a) The proposed zwitterionic resonance forms are similar to the principal resonance forms of the carbanion intermediate in transamination reactions; see: Martell, A. E. Acc. Chem. Res. 1989, 22, 115.
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    • note
    • (b) For the zwitterionic resonance forms of azomethine ylides, also see: 16a, 16b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.