Asymmetric 1,4-Addition of Arylboronic Acids to .ALPHA.,.BETA.-Unsaturated N-Acylamides Catalyzed by Dicationic Palladium(II)-(S,S)-Chiraphos Complex

• Nishikata Takashi

  Innovation Plaza Hokkaido, Japan Science and Technology Agency

• Yamamoto Yasunori

  Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University

• Miyaura Norio

  Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University

Bibliographic Information

Other Title

• Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated <i>N</i>-Acylamides Catalyzed by Dicationic Palladium(II)–(<i>S</i>,<i>S</i>)-Chiraphos Complex

Abstract

Palladium-catalyzed 1,4-addition of arylboronic acids to unsaturated carbonyl compounds has been limitedly used for ketone and aldehyde derivatives. It was found that reaction with N-acylamides exceptionally proceeds with high yields and high enantioselectivities. A dicationic palladium–chiraphos catalyst 3 gave optically active β-arylamides of up to 98% ee.

Journal

• Chemistry Letters

  Chemistry Letters 36 (12), 1442-1443, 2007

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390282679561283840
• NII Article ID: 10020011763
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2007.1442
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/36/12/1442/55595395/cl.2007.1442.pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed