Stereoselectivities of histidine-catalyzed asymmetric aldol additions and contrasts with proline catalysis: A quantum mechanical analysis

Journal of the American Chemical Society

Volumn 134, Issue 14, 2012, Pages 6286-6295

  Lam, Yu Hong ^a   Houk, K N ^a   Scheffler, Ulf ^b   Mahrwald, Rainer ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL ADDITION; ALDOL REACTIONS; ALDOLIZATION; C-C BONDS; DIASTEREO- AND ENANTIOSELECTIVITY; HYDROGEN-BOND DONORS; IMIDAZOLIUM; QUANTUM MECHANICAL ANALYSIS; QUANTUM-MECHANICAL CALCULATION; STEREOCHEMICAL MODELS; TRANSITION STATE;

ALDEHYDES; CARBOXYLIC ACIDS; CATALYSIS; HYDROGEN; QUANTUM THEORY; STEREOSELECTIVITY;

AMINO ACIDS;

ALDEHYDE DERIVATIVE; CARBOXYLIC ACID; HISTIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; PROLINE DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CONFORMATION; ELECTROPHILICITY; HYDROGEN BOND; NUCLEOPHILICITY; QUANTUM MECHANICS; STEREOCHEMISTRY;

ALDEHYDES; CARBON; CARBOXYLIC ACIDS; HISTIDINE; HYDROGEN BONDING; IMIDAZOLES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROLINE; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 84859567435     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2118392     Document Type: Article

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