Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence

Journal of the American Chemical Society

Volumn 131, Issue 38, 2009, Pages 13628-13630

  Lathrop, Stephen P ^a   Rovis, Tomislav ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CARBENES; CHEMICAL EQUATIONS; DICARBONYLS; DIKETONES; FUNCTIONALIZED; HIGH ENANTIOSELECTIVITY; KETO ESTER; MICHAEL ADDITIONS; N-HETEROCYCLIC CARBENES; ONE POT; SECONDARY AMINES; STARTING MATERIALS; UNSATURATED ALDEHYDES;

ADDITION REACTIONS; AMINES; ENANTIOSELECTIVITY; ESTERS; KETONES;

ALDEHYDES;

ALKYL GROUP; AMINE; BENZOIN; CARBENE; CYCLOPENTANONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; ONE POT SYNTHESIS; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

AMINES; CATALYSIS; CYCLOPENTANES; METHANE; STEREOISOMERISM;

EID: 70349745425     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905342e     Document Type: Article

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53. See Supporting Information.
54. 2O (∼10 mL), and then concentrated in vacuo. The resulting crude product was purified by flash silica gel chromatography.
55. Reaction of 4a and 8a was conducted on 2.4 mmol scale using 10 mol % 5, 5 mol % 6, and 5 mol % NaOAc to afford 90% yield, 91% ee, and identical diastereomer ratio of 10a.