On the mechanism of asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by QUINOX, a chiral isoquinoline N-oxide

Journal of the American Chemical Society

Volumn 130, Issue 15, 2008, Pages 5341-5348

  Malkov, Andrei V ^a   Ramírez López, Pedro ^a,d   Biedermannová, Lada ^a,b   Rulíšek, Lubomír ^b   Dufková, Lenka ^a,c   Kotora, Martin ^c   Zhu, Fujiang ^a   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

^d INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLTRICHLOROSILANES; ASYMMETRIC ALLYLATION; CROTYLATION; QUANTUM CHEMICAL CALCULATIONS;

ALLYL RESINS; AROMATIC COMPOUNDS; ASYMPTOTIC ANALYSIS; CATALYST ACTIVITY; COMPUTATIONAL COMPLEXITY; QUANTUM CHEMISTRY;

ALDEHYDES;

ALDEHYDE; ALDEHYDE DERIVATIVE; ALLYLTRICHLOROSILANE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CROTYLTRICHLOROSILANE; ISOQUINOLINE 2 OXIDE; ISOQUINOLINE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; QUANTUM MECHANICS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 42149130246     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja711338q     Document Type: Article

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106. 3 increase of the reaction rate, which is in agreement with the experimental observations.
107. - ion, which has to be taken into account in the dissociative reaction mechanism; however, this factor is unlikely to affect the overall picture significantly.
108. -1.
109. disp = -1.1.
110. -1. In the real system, the difference in arene-arene interactions energies for (R)- and (S)-manifolds is expected to further increase.
111. -1.