Enantioselective synthesis of a-quaternary amino acid derivatives by sequential enzymatic desymmetrization and curtius rearrangement of α,α-disubstituted malonate diesters

Journal of Organic Chemistry

Volumn 75, Issue 5, 2010, Pages 1612-1619

  Iosub, Violeta ^a   Haberl, Anton R ^a   Leung, Jennifer ^a   Tang, Michael ^a   Vembaiyan, Kannan ^a   Parvez, Masood ^a   Back, Thomas G ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; AMINO ACID DERIVATIVES; AMINO ESTERS; ARYLATIONS; BENZYL ALCOHOL; CHIRAL AMINES; DESYM-METRIZATION; DIESTERS; DIMETHYL MALONATE; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE SYNTHESIS; ENZYMATIC DESYMMETRIZATIONS; HIGH YIELD; MALONATES; PORCINE LIVER ESTERASE; QUATEMARY; SPECIFIC ROTATIONS;

AMINES; AMINO ACIDS; ESTERIFICATION; ESTERS; HYDROCARBONS; ORGANIC ACIDS; UREA; X RAY CRYSTALLOGRAPHY;

AMINATION;

2 BENZYL 2 ETHYLMALONIC ACID MONOMETHYLESTER; 2 BUTYL 2 (2 PHENETHYL)MALONIC ACID MONOMETHYLESTER; 2 CYCLOHEXYL 2 METHYLMALONIC ACID MONOMETHYLESTER; 2 CYCLOHEXYLMETHYL 2 ETHYLMALONIC ACID MONOMETHYLESTER; 2 ETHYL 2 (2 PHENETHYL)MALONIC ACID MONOMETHYLESTER; 2 HEXYL 2 METHYLMALONIC ACID MONOMETHYLESTER; 2 ISOPROPYL 2 METHYLMALONIC ACID MONOMETHYLESTER; 2 METHYL 2 (2 PHENETHYL)MALONIC ACID MONOMETHYLESTER; 2 METHYL 2 PHENYLLMALONIC ACID MONOMETHYLESTER; 2 METHYL 2 PROPARGYLMALONIC ACID MONOMETHYLESTER; ALKYL GROUP; ALPHA,ALPHA MALONATE DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; BENZYL ALCOHOL; BENZYL DERIVATIVE; CYCLOALKYL; DIMETHYL 2 (2 PHENETHYL) 2 PROPYLMALONATE; DIMETHYL 2 BENZYL 2 PROPYLMALONATE; DIMETHYL 2 BUTYL 2 (2 PHENETHYL)MALONATE; DIMETHYL 2 CYCLOHEXYL 2 METHYLMALONATE; DIMETHYL 2 CYCLOHEXYLMETHYL 2 ETHYLMALONATE; DIMETHYL 2 ETHYL 2 (2 PHENETHYL)MALONATE; DIMETHYL 2 METHYL 2 (2 PHENETHYL)MALONATE; ESTER; ESTER DERIVATIVE; MALONIC ACID; METHYLTESTOSTERONE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; UREA; AMINO ACID; ESTERASE; MALONIC ACID DERIVATIVE; METHYLMALONIC ACID;

ALKYLATION; ARTICLE; ARYLATION; CHIRALITY; CONTROLLED STUDY; CURTIUS REARRANGEMENT; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; PROTEIN QUATERNARY STRUCTURE; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY; BIOCHEMISTRY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ALKYLATION; AMINES; AMINO ACIDS; BIOCHEMICAL PROCESSES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ESTERASES; ESTERS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MALONATES; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 77949310221     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902584r     Document Type: Article

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