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Volumn 68, Issue 3, 2003, Pages 1107-1116

Enantioselective [6π]-photocyclization reaction of an acrylanilide mediated by a chiral host. Interplay between enantioselective ring closure and enantioselective protonation

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SOLVENTS; TOLUENE; X RAY CRYSTALLOGRAPHY;

EID: 0037423365     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026602d     Document Type: Article
Times cited : (81)

References (87)
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    • note
    • The equilibrium between the cis and trans rotamers of compound 1a is in favor of the trans rotamer, which complicates any attempt to determine the complex formation quantitatively. NMR titration experiments were not conclusive. In addition, as one referee suggested, the photoexcited cis rotamer (being a stronger acid and a stronger base after photoexcitation) might be trapped in complex 4· 1a and consequently end up as 4·ent-8.
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