Virtually complete control of simple and face diastereoselectivity in the Michael addition reactions between achiral equivalents of a nucleophilic glycine and (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Practical method for preparation of β-substituted pyroglutamic acids and prolines

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 4984-4990

  Soloshonok, Vadim A ^a   Ueki, Hisanori ^a   Tiwari, Rohit ^a   Cai, Chaozhong ^b   Hruby, Victor J ^b  

^a UNIVERSITY OF OKLAHOMA   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; COMPLEXATION; ORGANOMETALLICS; STEREOCHEMISTRY;

MICHAEL ADDITION REACTIONS; SCHIFF BASES;

AMINO ACIDS;

2 (N ALPHA PICOLYLAMINO)ACETOPHENONE; 4 PHENYL 1,3 OXAZOLIDIN 2 ONE DERIVATIVE; ACETOPHENONE DERIVATIVE; BASE; CARBON; CARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID; GLUTAMINE; GLYCINE; NICKEL COMPLEX; ORGANIC COMPOUND; OXAZOLIDINE DERIVATIVE; PROLINE; PYROGLUTAMIC ACID; SCHIFF BASE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHIRALITY; DIASTEREOISOMER; INTERMETHOD COMPARISON; MICHAEL ADDITION; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

GLYCINE; MOLECULAR STRUCTURE; PROLINE; PYRROLIDONECARBOXYLIC ACID; STEREOISOMERISM;

EID: 3543014960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0495438     Document Type: Article

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