Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives

Journal of the American Chemical Society

Volumn 128, Issue 6, 2006, Pages 1810-1811

  Bekele, Tefsit ^a   Shah, Meha H ^a   Wolfer, Jamison ^a   Abraham, Ciby J ^a   Weatherwax, Anthony ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMPHOLYTE; BENZOYLQUINIDINE; BETA LACTAM; BETA LACTONE; BUTYRYL CHLORIDE; CARBOXYLIC ACID DERIVATIVE; CHLORANIL; CHLORIDE; CINCHONA ALKALOID; DIHYDROCINNAMOYL CHLORIDE; IMINE; KETENE DERIVATIVE; KETENE ENOLATE; LACTONE; MANDELIC ACID; PHENANTHRENEQUINONE; PHENYLACETYL CHLORIDE; QUINIDINE; QUINONE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DEPROTECTION REACTION; ENANTIOSELECTIVITY; HALOGENATION; HYDROXYLATION; OXIDATION; SOLVENT EFFECT; STOICHIOMETRY; TEMPERATURE DEPENDENCE;

CARBOXYLIC ACIDS; CATALYSIS; CHLORANIL; CYCLIZATION; ETHYLENES; KETONES; OXIDATION-REDUCTION; QUINONES; STEREOISOMERISM;

EID: 33244481980     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058077g     Document Type: Article

References (23)

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22. o-Bromanil was added slowly to the reaction mixture over 6 h.
23. Absolute configurations of the products were determined by conversion to the corresponding α-hydroxyesters of known configuration through sequential methanolysis/CAN oxidation. See Supporting Information for details.