Asymmetric synthesis of pyrrolo[2,1-a]isoquinoline derivatives by 1,3-dipolar cycloadditions of stabilized isoquinolinium N-ylides with sulfinyl dipolarophiles

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3296-3305

  García Ruano, José Luis ^a   Fraile, Alberto ^a   Martín, M Rosario ^a   González, Gemma ^a   Fajardo, Cristina ^a   Martín Castro, Ana María ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-CONFORMATIONS; ASYMMETRIC SYNTHESIS; AZOMETHINE YLIDES; DIPOLAR CYCLOADDITIONS; DIPOLAROPHILES; ENANTIOPURE; FACIAL SELECTIVITY; ISOQUINOLINES; SULFINYL GROUP;

CYCLOADDITION; SULFUR;

FUNCTIONAL GROUPS;

ISOQUINOLINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

ISOQUINOLINES; NITROGEN; PYRROLES; QUINOLINIUM COMPOUNDS; SULFOXIDES;

EID: 79955557380     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200191c     Document Type: Article

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79. CCDC809009, CCDC809010, and CCDC809011 contain the supplementary crystallographic data for anti-endo-21a, anti-endo-21b, and syn-endo-21a, respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data-request/cif, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223.
80. The reactions of ylide 1 with sulfinylfuranones 7 were assayed in different solvents. Unfortunately, the reaction mixtures obtained in less polar solvent than acetonitrile (toluene or dichloromethane) were complex and any certain conclusion can be inferred.