A facile and stereocontrolled synthesis of γ-substituted γ-fluoroglutamates by conjugate addition: Conflicting effect between fluorinated enaminoester and hinderered Michael acceptor

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7596-7604

  Drège, Emmanuelle ^a,b   Guillaume, Anaïs ^a,b   Boukhedimi, Nadjia ^a,b   Marrot, Jéroâme ^c   Troufflard, Claire ^a   Tran Huu Dau, Marie Elise ^d   Joseph, Delphine ^a,b   Delarue Cochin, Sandrine ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b IPSIT   (France)

^c UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^d CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1-PHENYLETHYLAMINE; AB INITIO COMPUTATIONS; ACID FUNCTION; ASYMMETRIC CONJUGATE ADDITION; CONJUGATE ADDITION; DESTABILIZING EFFECT; DIASTEREO-SELECTIVITY; DIASTEREOMERIC; ELECTROPHILES; ENAMINOESTER; FLUORINE ATOMS; METHYL ACRYLATES; MICHAEL ACCEPTORS; MICHAEL ADDITIONS; NATURAL CONFIGURATIONS; QUATERNARY CARBON; STEREOCONTROL; STEREOCONTROLLED SYNTHESIS; TERTIARY CENTERS;

ADDITION REACTIONS; AMINO ACIDS; ENANTIOSELECTIVITY; FLUORINE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ORGANIC POLYMERS;

2 FLUOROENAMINOESTER; 4 FLUOROGLUTAMIC ACID; ACRYLIC ACID METHYL ESTER; ALPHA METHYLBENZYLAMINE; AMINO ACID; BETA ENAMINOESTER; CARBON; ELECTROPHILE; ESTER DERIVATIVE; FLUORINE; GLUTAMIC ACID DERIVATIVE; METHYL ALPHA ACETAMIDOACRYLATE; NUCLEOPHILE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ADDITION REACTION; ARTICLE; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; ENTHALPY; FLUORINE NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALANINE; CATALYSIS; FLUORINE; GLUTAMATES; HALOGENATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 78449253772     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101417c     Document Type: Article

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