Organocatalyzed enantioselective protonation of silyl enol ethers: Scope, limitations, and application to the preparation of enantioenriched homoisoflavones

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7704-7716

  Poisson, Thomas ^a   Gembus, Vincent ^a   Dalla, Vincent ^b   Oudeyer, Sylvain ^a   Levacher, Vincent ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

^b UNIVERSITÉ DU HAVRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; ECO-FRIENDLY; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; NITROGEN BASIS; ORGANOCATALYTIC; PROTIC NUCLEOPHILES; PROTON SOURCE; RELEVANT REACTIONS; SILYL ENOL ETHERS; SYNTHETIC UTILITY;

ENANTIOSELECTIVITY; ETHERS; ORGANIC COMPOUNDS;

PROTONATION;

2 ALLYL 6 METHOXY 1 TRIMETHYLSILYLOXYTETRAL 1 ENE; 2 BENZYL 6 METHOXY 1 TRIMETHYLSILYLOXYTETRAL 1 ENE; 2 BENZYL 7 METHOXY 1 TRIMETHYLSILYLOXY TETRAL 1 ENE; 2 METHYL 1 [(CHLOROMETHYLDIMETHYL)SILYLOXY]TETRAL 1 ENE; 2 METHYL 1 TRIETHYLSILYLOXYTETRAL 1 ENE; 2 METHYL 6 METHOXY 1 TRIMETHYLSILYLOXYTETRAL 1 ENE; 8 METHYL 9 TRIMETHYLSILYLOXY 6,7 DIHYDRO [5H] BENZOCYCLOHEPTENE; BRONSTED BASE; ETHER DERIVATIVE; HOMOISOFLAVONE DERIVATIVE; ISOFLAVONE DERIVATIVE; NUCLEOPHILE; SILYL ENOL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PROTON TRANSPORT; SYNTHESIS;

CATALYSIS; CINCHONA ALKALOIDS; ETHERS; ISOFLAVONES; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 78449252047     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101585t     Document Type: Article

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