Transition-state charge stabilization through multiple non-covalent interactions in the guanidinium-catalyzed enantioselective claisen rearrangement

Journal of the American Chemical Society

Volumn 133, Issue 13, 2011, Pages 5062-5075

  Uyeda, Christopher ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL FRAGMENTS; CHARGE STABILIZATION; CLAISEN REARRANGEMENT; ENANTIOSELECTIVE; GUANIDINIUM; KETO ESTER; MECHANISTIC ANALYSIS; NEGATIVE CHARGE; NON-COVALENT INTERACTION; TRANSITION STATE;

CATALYSTS; ESTERS; ETHERS; STABILIZATION;

ENANTIOSELECTIVITY;

4 DIMETHYLAMINOPHENYL; ALLYL COMPOUND; AMINOPHENOL DERIVATIVE; AROMATIC COMPOUND; ARYLPYRROLE; CATION; ESTER DERIVATIVE; GUANIDINE; HYDROGEN; O ALLYL ALPHA KETOESTER; OXALLYL; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CLAISEN REARRANGEMENT; CONTROLLED STUDY; ENANTIOSELECTIVITY; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; PHASE TRANSITION; QUANTITATIVE ANALYSIS; SUBSTITUTION REACTION;

BACILLUS SUBTILIS; CATALYSIS; CHORISMATE MUTASE; CRYSTALLOGRAPHY, X-RAY; ESTERS; GUANIDINE; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 79953879649     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110842s     Document Type: Article

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