Enantioselective cyanosilylation of ketones catalyzed by a chiral oxazaborolidinium ion

Journal of the American Chemical Society

Volumn 127, Issue 15, 2005, Pages 5384-5387

  Do, Hyun Ryu ^b   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

^b Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; BORON COMPOUNDS; CATALYSIS; HYDROGEN BONDS; KETONES; REACTION KINETICS; SALTS;

CO-REACTANTS; CYANOSILYLATION; ENANTIOSELECTIVE REACTIONS; OXAZABOROLIDINIUM SALT;

CATALYSTS;

ACETONE; ALDEHYDE; CARBON; CARBONYL DERIVATIVE; DIPHENYLMETHYLPHOSPHINE OXIDE; HYDROGEN; KETONE; OXAZABOROLIDINE DERIVATIVE; OXAZABOROLIDINIUM; OXYGEN; PHOSPHINE OXIDE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYLCYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHIRALITY; CYANOSILYLATION; ENANTIOSELECTIVITY; HYDROGEN BOND; MECHANICS; REACTION ANALYSIS;

EID: 17644414916     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050543e     Document Type: Article

References (18)

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11. The earlier the transition state in the 1,2-addition to the complexed carbonyl, the greater the attractive interaction between carbonyl and neighboring mexyl groups and the greater the degree of organization of the reactants as shown in Table 1, entry 6.
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16. Higher enantioselectivities were observed with an o-tolyl substituent on boron relative to phenyl, methyl, or n-alkyl.
17. In the absence of phosphine oxide as co-reactant the enantioselectivities were considerably lower.
18. Data on the determination of enantioselectivities and absolute configurations of the cyanosilylation products are provided in the Supporting Information.