Allylation of Ketones with a Ferrocene-Based Planar Chiral Lewis Acid

Allylation of Ketones with a Ferrocene-Based Planar Chiral Lewis Acid

Flat, like your hand: The heteronuclear bidentate Lewis acid 1,2‐Fc(BMeCl)(SnMe2Cl) is readily resolved into its constituent enantiomers through highly stereoselective complexation with N‐methylpseudoephedrine. The resulting planar chiral Lewis acids show optical purities greater than 97 % and, upon...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-01, Vol.47 (6), p.1134-1137
Hauptverfasser: Boshra, Ramez, Doshi, Ami, Jäkle, Frieder
Format: Artikel
Sprache:eng
Schlagworte:
allylation
boron
chirality
ferrocene
organoboranes
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Zusammenfassung:Flat, like your hand: The heteronuclear bidentate Lewis acid 1,2‐Fc(BMeCl)(SnMe2Cl) is readily resolved into its constituent enantiomers through highly stereoselective complexation with N‐methylpseudoephedrine. The resulting planar chiral Lewis acids show optical purities greater than 97 % and, upon conversion to the respective allylborane derivatives (see scheme), rapidly add to ketones with enantiomeric excess of up to 80 %.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200704687