Improved and efficient synthesis of chiral N,P-ligands via cyclic sulfamidates for asymmetric addition of butyllithium to benzaldehyde.
A robust and scaleable route to chiral 1-isopropylamino-2-(diphenylphosphino)ethanes is described via the ring-opening of chiral, cyclic sulfamidates with potassium diphenylphosphide (KPPh(2)). The novel protocol offers a robust access to gram quantities of chiral amino phosphinoethanes in high yields. The Li-amides of the chiral aminophosphines were evaluated as chiral ligands in the asymmetric addition of n-butyllithium (BuLi) to benzaldehyde, yielding 1-phenylpentanol up to 98% ee.
Rönnholm
Petra
P
Department of Chemistry, Göteborg University, Kemivägen 10, SE-412 96 Göteborg, Sweden.
Södergren
Mikael
M
Hilmersson
Göran
G
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
D000577:Amides; D001547:Benzaldehydes; D001897:Boronic Acids; D008024:Ligands; D009942:Organometallic Compounds; C046771:butyllithium; D010758:Phosphorus; D002713:Chlorine; D013455:Sulfur; D009584:Nitrogen; C032175:benzaldehyde