Michael addition reactions between chiral equivalents of a nucleophilic glycine and (S)- or (R)-3-[(E)-enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a general method for efficient preparation of β-substituted pyroglutamic acids. Case of topographically controlled stereoselectivity

Journal of the American Chemical Society

Volumn 127, Issue 43, 2005, Pages 15296-15303

  Soloshonok, Vadim A ^a   Cai, Chaozhong ^b   Yamada, Takeshi ^a,c   Ueki, Hisanori ^a   Ohfune, Yasufumi ^c   Hruby, Victor J ^b  

^a UNIVERSITY OF OKLAHOMA   (United States)

^b University of Arizona   (United States)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; COMPLEXATION; ENZYMES; NICKEL COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

GLYCINE; MICHAEL ACCEPTORS; MICHAEL ADDITION REACTION; SCHIFF BASE;

ADDITION REACTIONS;

2 [N (N BENZYLPROLYL)AMINO]BENZOPHENONE; 3 (ENOYL) 4 PHENYL 1,3 OXAZOLIDIN 2 ONE DERIVATIVE; BENZOPHENONE DERIVATIVE; GLYCINE; NICKEL COMPLEX; OXAZOLIDINONE DERIVATIVE; PYROGLUTAMIC ACID; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; MICHAEL ADDITION; REACTION TIME; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; GLYCINE; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NICKEL; OXAZOLIDINONES; PYRROLIDONECARBOXYLIC ACID; SCHIFF BASES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEREOISOMERISM;

EID: 27544463710     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0535561     Document Type: Article

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