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Titolo:
New auxiliaries for copper-catalyzed asymmetric Michael reactions: Generation of quaternary stereocenters at room temperature
Autore:
Christoffers, J; Mann, A;
Indirizzi:
Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany Univ Stuttgart Stuttgart Germany D-70569 hem, D-70569 Stuttgart, Germany Tech Univ Berlin, Inst Organ Chem, Sekretariat C3, D-10623 Berlin, GermanyTech Univ Berlin Berlin Germany D-10623 riat C3, D-10623 Berlin, Germany
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 5, volume: 7, anno: 2001,
pagine: 1014 - 1027
SICI:
0947-6539(20010302)7:5<1014:NAFCAM>2.0.ZU;2-I
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-KETO-ESTERS; CHIRAL DIPHOSPHINE LIGAND; ALPHA-AMINO-ACIDS; 1,3-DICARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; DIASTEREOSELECTIVE REDUCTION; STEREOSELECTIVE REACTIONS; CARBON CENTERS; ENAMINO ESTERS; BINOL COMPLEX;
Keywords:
amino acids; asymmetric catalysis; chiral auxiliaries; copper; Michael additions;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
76
Recensione:
Indirizzi per estratti:
Indirizzo: Christoffers, J Univ Stuttgart, Inst Organ Chem, Pfaffenwaldring 55, D-70569 Stuttgart, Germany Univ Stuttgart Pfaffenwaldring 55 Stuttgart Germany D-70569
Citazione:
J. Christoffers e A. Mann, "New auxiliaries for copper-catalyzed asymmetric Michael reactions: Generation of quaternary stereocenters at room temperature", CHEM-EUR J, 7(5), 2001, pp. 1014-1027

Abstract

Dialkyl amides of L-valine, L-isoleucine, and L-tert-leucine (2) are excellent chiral auxiliaries for the construction of quaternary stereocenters atambient temperature. Enaminoesters 3, prepared from these auxiliaries 2 and Michael donors 1, undergo a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone (MVK, 4) to afford products 5 in 70-90% yield and 90-99% ee (enantiomeric excess). The exclusion of moisture or oxygen is notnecessary. The auxiliaries 2 are readily available by standard procedures. After workup they can be recovered almost quantitatively.

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Documento generato il 02/04/20 alle ore 12:25:37