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Titolo:
Synthesis of enantiomerically enriched allenes by (-)-sparteine-mediated lithiation of alkynyl carbamates
Autore:
Schultz-Fademrecht, C; Wibbeling, 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:
ORGANIC LETTERS
fascicolo: 8, volume: 3, anno: 2001,
pagine: 1221 - 1224
SICI:
1523-7060(20010419)3:8<1221:SOEEAB>2.0.ZU;2-2
Fonte:
ISI
Lingua:
ENG
Soggetto:
METALATED NITROGEN DERIVATIVES; CLAISEN REARRANGEMENT; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; ENANTIOSELECTIVE LITHIATION; STEREOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; CARBONIC-ACID; SUBSTITUTION; COMPLEXES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
52
Recensione:
Indirizzi per estratti:
Indirizzo: Hoppe, D Univ Munster, Inst Organ Chem, Corremsstr 40, D-48149 Munster, Germany Univ Munster Corremsstr 40 Munster Germany D-48149 ster, Germany
Citazione:
C. Schultz-Fademrecht et al., "Synthesis of enantiomerically enriched allenes by (-)-sparteine-mediated lithiation of alkynyl carbamates", ORG LETT, 3(8), 2001, pp. 1221-1224

Abstract

The alpha -deprotonation of alkynyl carbamates 3 with the chiral base (-)-sparteine (4)/n-butyllithium, transmetalation with CITi((OPr)-Pr-/)B-3 and subsequent substitution with an aldehyde results in the formation of enantioenriched 4-hydroxyallenyl carbamates 11. Stereoselection is determined by dynamic resolution of the lithium/(-)-sparteine complexes by selective crystallization.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 10:57:00