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Titolo:
Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis ofproline and pipecolic acid derivatives
Autore:
Davis, FA; Zhang, HM; Lee, SH;
Indirizzi:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA Temple Univ Philadelphia PA USA 19122 pt Chem, Philadelphia, PA 19122 USA
Titolo Testata:
ORGANIC LETTERS
fascicolo: 5, volume: 3, anno: 2001,
pagine: 759 - 762
SICI:
1523-7060(20010308)3:5<759:MOS(II>2.0.ZU;2-B
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA-AMINO-ACIDS; THIOOXIME S-OXIDES; AMIDE ISOMER EQUILIBRIUM; STEREOSELECTIVE SYNTHESIS; ENANTIOPURE SULFINIMINES; CONFORMATIONAL-ANALYSIS; STRECKER SYNTHESIS; ENANTIOSPECIFIC SYNTHESIS; ALKALOID SYNTHESIS; ESTERS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
47
Recensione:
Indirizzi per estratti:
Indirizzo: Davis, FA Temple Univ, Dept Chem, Philadelphia, PA 19122 USA Temple Univ Philadelphia PA USA 19122 hiladelphia, PA 19122 USA
Citazione:
F.A. Davis et al., "Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis ofproline and pipecolic acid derivatives", ORG LETT, 3(5), 2001, pp. 759-762

Abstract

[GRAPHICS]On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha -amino nitriles that afford oxo alpha -amino acids on hydrolysis. These amino acidscyclize and are reduced to cis proline and cis pipecolic acids derivativesin high ee and good yield. This new procedure avoids many of the limitations related to the preparation of oxo amino acids from proteinogenic amino acids.

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Documento generato il 31/03/20 alle ore 21:44:25