Reaction pathway and stereoselectivity of asymmetric synthesis of chrysanthemate with the Aratani C1-symmetric salicylaldimine-copper catalyst

Journal of the American Chemical Society

Volumn 126, Issue 23, 2004, Pages 7271-7280

  Suenobu, Katsuhiro ^a   Itagaki, Makoto ^a   Nakamura, Eiichi ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER; HYDROGEN BONDS; PROBABILITY DENSITY FUNCTION; STRUCTURE (COMPOSITION);

CARBENE; CYCLOPROPANATION;

ESTERS;

2,5 DIMETHYL 2,4 HEXADIENE; CARBENE; CARBONYL DERIVATIVE; CHRYSANTHEMATE; CHRYSANTHEMIC ACID METHYL ESTER; CYANIDIN 3 GLUCOSIDE; METHYL DIAZOACETATE; SALICYLALDEHYDE; SALICYLALDIMINE COPPER COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CONFORMATION; CYCLOPROPANATION; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR MODEL; MOLECULAR ORBITAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 2942590316     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031524c     Document Type: Article

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50. carbene bond were calculated for the model below, where the intramolecular hydrogen bonding is neglected. The calculated free energy barriers are 12.3 and 13.2 kcal/ mol (two maxima owing to the relative orientation of the side chain and the ester group) by single-point calculations at the B3LYP/6-311+G(d,p) level with the optimized geometries and frequencies at the B3LYP/6-31 G(d) level. For comparison, the free energy barriers for the cyclopropanation were also calculated at the same level. For instance, those for 23 and 26 in Figure 6 are 12.9 and 12.1 kcal/mol, respectively. It may be noted that the comparable levels of the two activation energies obtained by the theoretical/ chemical model does not rigorously satisfy the Curtin-Hammet conditions that are assumed in the present study. Equation presented.
51. The enantioselectivity calculated for the energy differences of the TSs at the B3LYP/6-311+G(d, p)//B3LYP/6-31G(d)+3-21G level was (+):(-) = 76.0:24.0 (Boltzmann distribution at 298 K), the same trend as in the text. The one based on the stability of the carbene complexes at the same level was (+):(-) = 28.8: 71.2, the trend again the same as in the text and hence contradictory with the experimental data. The original data on these one-point energies are shown in Figure S4 in Supporting Information.
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