Palladium(II)-catalyzed 1,4-addition of arylboronic acids to β-arylenals for enantioselective syntheses of 3,3-diarylalkanals: a short synthesis of (+)-(R)-CDP 840

• Nishikata, Takashi

• Yamamoto, Yasunori

• Miyaura, Norio

Abstract

Table Schem Fig Revised

1,4-Addition of arylboronic acid to trans-β-arylenals proceeded smoothly in acetone–water (10/1) at 10–25 °C in the presence of [Pd(S,S-chiraphos)(PhCN)2](SbF6)2 (0.5 mol %), AgX (X = BF4, SbF6, 10 mol %) and aqueous 42% HBF4 to afford optically active 3,3-diarylalkanals with high enantioselectivities in a range of 86–97% ee. The protocol provided a method for short-step synthesis of optically active (+)-(R)-CDP 840.

Journal

• Tetrahedron Letters

  Tetrahedron Letters 48 (23), 4007-4010, 2007-06-04

  Elsevier Ltd.

Keywords

• Conjugate addition
• Asymmetric synthesis
• Asymmetric catalyst
• Arylboronic acid
• Chiral aldehydes

Details

• CRID: 1050001338990641536
• NII Article ID: 120000972381
• HANDLE: 2115/28004
• ISSN: 00404039
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles