Deslongchamps annulations with benzoquinone monoketals

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6524-6527

  Petrović, Denis ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; BENZOQUINONE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; KETONE; SPIRO COMPOUND; SPIRONOLACTONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZOQUINONES; CATALYSIS; CYCLOHEXANONES; KETONES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; SPIRONOLACTONE; STEREOISOMERISM;

EID: 84055178168     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202809y     Document Type: Article

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74. CCDC849007 (35a), 849008 (38a), and 849006 (38b) contain the crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via the link www.ccdc.cam.ac.uk/data-request/cif
75. This conclusion is not only based on a plausible analogy but also on circumstantial 1H NMR evidence. In CDCl3 solutions 8a-H is significantly deshielded (35a: δ = 3.40 ppm; 35b: δ = 3.43 ppm; 35c: δ=3.39 ppm; 35d: δ=4.05-4.10 ppm (includes deshielding effect of Rphenyl group); 37: δ=3.22 ppm) compared to 5-H (35a: δ=2.79 ppm; 35b: δ = 2.68 ppm; 35c: δ = 2.58 ppm; 35d: δ = 3.48 ppm (includes deshielding effect of R-phenyl group); 37: δ = 2.56-2.68 ppm). This indicates that 8a-H is cis-oriented and 4-H trans-oriented relative to the ester substituent at C-4a.
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