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Titolo:
Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via (-)-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation
Autore:
Laqua, H; Frohlich, R; Wibbeling, B; 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:
JOURNAL OF ORGANOMETALLIC CHEMISTRY
fascicolo: 1-2, volume: 624, anno: 2001,
pagine: 96 - 104
SICI:
0022-328X(20010401)624:1-2<96:SOEIBA>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
CHIRAL DISUBSTITUTED CYCLOPROPANES; BENZYLIC ORGANOZINC HALIDES; INTRAMOLECULAR CARBOLITHIATION; ENANTIOSELECTIVE SYNTHESIS; CONFIGURATIONAL STABILITY; (-)-SPARTEINE-ASSISTED DEPROTONATION; ASYMMETRIC CYCLOCARBOLITHIATION; CINNAMYL DERIVATIVES; CARBANION CENTER; CYCLIZATION;
Keywords:
chiral carbanions; cyclocarbolithiation; (-)-sparteine; kinetic resolution; lithiated alkyl carbamates;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
45
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:
H. Laqua et al., "Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via (-)-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation", J ORGMET CH, 624(1-2), 2001, pp. 96-104

Abstract

By treatment of the racemic 3-(indenyl)alkyl carbamate rac-8 with sec-BuLi-(-)-sparteine, cyclocarbolithiation occurs, which is accompanied by kinetic resolution during the cyclisation step. After addition of electrophiles, the stereohomogeneous optically active benzobicyclo[3.3.0]octenols of type 13 are obtained. Increasing the temperature from - 78 to - 40 degreesC or the application of TMEDA instead of (-)-sparteine yields the formation of the tricyclic cyclopropane 14. (C) 2001 Elsevier Science B.V. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 18/01/20 alle ore 13:33:52