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

Abstract An asymmetric 1,4-addition of arylboronic acids to RCH=CHCO 2 Ar (Ar = Ph or 4-acetylphenyl) was carried out at 50 ˚C in aqueous acetone in the presence of [Pd(chiraphos)(PhCN) 2 ](SbF 6 ) 2 . The reaction gave optically active β-aryl esters in up to 98% ee. The protocol provided a simple a...

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Bibliographic Details
Published in:Synlett 2008-10, Vol.2008 (16), p.2487-2490
Main Authors: Nishikata, Takashi, Kiyomura, Shunsuke, Yamamoto, Yasunori, Miyaura, Norio
Format: Article
Language:English
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Summary:Abstract An asymmetric 1,4-addition of arylboronic acids to RCH=CHCO 2 Ar (Ar = Ph or 4-acetylphenyl) was carried out at 50 ˚C in aqueous acetone in the presence of [Pd(chiraphos)(PhCN) 2 ](SbF 6 ) 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2008-1078259