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Titolo:
Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active beta-amino alcohols via 1-oxy-substituted alkyllithium intermediates
Autore:
Schwerdtfeger, J; Kolczewski, S; Weber, B; Frohlich, R; Hoppe, D;
Indirizzi:
Univ Munster, Inst Organ Chem, D-48149 Munster, Germany Univ Munster Munster Germany D-48149 rgan Chem, D-48149 Munster, Germany
Titolo Testata:
SYNTHESIS-STUTTGART
fascicolo: 9, , anno: 1999,
pagine: 1573 - 1592
SICI:
0039-7881(199909):9<1573:SDOCAA>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
C-13 SIDE-CHAIN; DIPOLE-STABILIZED CARBANIONS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; C-SUBSTITUTION; (-)-SPARTEINE-MEDIATED DEPROTONATION; (-)-SPARTEINE-ASSISTED DEPROTONATION; CHEMOENZYMATIC SYNTHESIS; PRACTICAL PREPARATION; KINETIC RESOLUTION;
Keywords:
2-amino-1-hydroxy carbanions; stereoselective deprotonation; chiral 2-aminoalkan-1-ols; (-)-sparteine; substituted isoserines;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
80
Recensione:
Indirizzi per estratti:
Indirizzo: Hoppe, D Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany Univ Munster Corrensstr 40 Munster Germany D-48149 ster, Germany
Citazione:
J. Schwerdtfeger et al., "Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active beta-amino alcohols via 1-oxy-substituted alkyllithium intermediates", SYNTHESIS-S, (9), 1999, pp. 1573-1592

Abstract

A facile protocol for the electrophilic C-substitution (methylation, acylation, alpha-hydroxyalkylation, and carboxylation) of several 2-(N,N-dibenzylamino)alkan-1-ols via the carbamates 10 is reported. The stereochemistry of the lithiation is greatly influenced by the complexing diamine. The substrate-directed selection be tween the diastereotopic alpha-pro-R and pro-S protons in the TMEDA-assisted deprotonation is largely shifted towards pro-S-selectivity in the presence of (-)-sparteine (4). Each of both diastereomeric series is readily accessible in several cases.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/01/20 alle ore 10:01:28