Enantioselective synthesis of hydrobenzofuranones using an asymmetric desymmetrizing intramolecular stetter reaction of cyclohexadienones

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 598-604

  Liu, Qin ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35948961858     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op600278f     Document Type: Article

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55. For example, 36 is ∼9.9 kJ/mol more stable than the diastereomer having the methyl group on the endo face of the bicycle, while 38 is ∼36 kJ/mol more stable than the diastereomer having the bulky tert-butyl in that position.
56. The use of propylene glycol in the starting material synthesis affords homologous substrates. These substrates undergo efficient Stetter reactions using achiral catalysts, but are much more prone to base-induced Michael cyclization in the presence of our suite of chiral catalysts. Efforts to remedy this situation are currently underway.