Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media

Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media

Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (>20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amp...

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Veröffentlicht in:Organic letters 2002-06, Vol.4 (12), p.2105-2108
Hauptverfasser: Lautens, Mark, Mancuso, John
Format: Artikel
Sprache:eng
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Zusammenfassung:Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (>20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amphos chloride, a sterically bulky, electron-rich, water-soluble phosphine ligand.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0260627