Diastereoselective intramolecular Friedel-Crafts alkylation of tetralins

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3000-3003

  Liébert, Clémence ^a   Brinks, Marion K ^a   Capacci, Andrew G ^a   Fleming, Matthew J ^b   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b SOLVIAS AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79958773834     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2008236     Document Type: Article

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34. It was mandatory to remove the double bond prior to the FC alkylation since the tetralin could easily aromatize in the presence of an acid source.
35. In this case, the major side product observed was the enamine, corresponding to the elimination of the alcohol functionality.
36. No ee could be determined as no suitable conditions could be found to achieve a desired peak separation.
37. 1H NOE experiments.
38. 3 was used as Lewis acid.
39. The reaction was carried out in dioxane at 80 °C for 20 h.
40. Substrate syn- 48 was prepared via an oxidation-reduction sequence starting from anti- 48.