Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction

Journal of the American Chemical Society

Volumn 128, Issue 8, 2006, Pages 2552-2553

  Liu, Qin ^a   Rovis, Tomislav ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXADIENONE; CYCLOHEXANE DERIVATIVE; FURANONE DERIVATIVE; HYDROBENZOFURANONE; IODINE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STETTER REACTION;

ALDEHYDES; BENZOFURANS; CYCLIZATION; CYCLOHEXANES;

EID: 33644661812     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058337u     Document Type: Article

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48. Lower catalyst loading or higher concentration results in comparable yields of product but lower enantioselectivity (2 mol % catalyst, 84% yield, 83% ee; 0.04 M, 90% yield, 88% ee).
49. Relative and absolute configurations determined by nOe and X-ray for several compounds and the rest assigned by analogy (see Supporting Information for details). We have been unable to form the complementary diastereomers even by base-induced epimerization. A semiempirical calculation of 23, 25, 27, and 29 suggests the minor diastereomers are as much as 9 kcal/mol less stable. Examination of GC traces suggests that this reaction is likely far more selective than 95% of a single diastereomer.