RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2008(16): 2487-2490
DOI: 10.1055/s-2008-1078259
DOI: 10.1055/s-2008-1078259
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Esters Catalyzed by Dicationic Palladium(II)-Chiraphos Complex for Short-Step Synthesis of SmithKline Beecham’s Endothelin Receptor Antagonist
Weitere Informationen
Publikationsverlauf
Received
13 June 2008
Publikationsdatum:
21. August 2008 (online)


Abstract
An asymmetric 1,4-addition of arylboronic acids to RCH=CHCO2Ar (Ar = Ph or 4-acetylphenyl) was carried out at 50 ˚C in aqueous acetone in the presence of [Pd(chiraphos)(PhCN)2](SbF6)2. The reaction gave optically active β-aryl esters in up to 98% ee. The protocol provided a simple access to an endothelin receptor antagonist reported by SmithKline Beecham.
Key words
arylboronic acids - palladium catalyst - asymmetric reaction - conjugate addition - β-arylalkanoate - bioactive compound