Enantioselective Diels–Alder Reaction Induced by Chiral Supramolecular Lewis Acid Catalysts Based on CN···B and PO···B Coordination Bonds

• Hatano, Manabu

• Hayashi, Kazushi

• Sakamoto, Tatsuhiro

• Makino, Yuma

• Ishihara, Kazuaki

Abstract

Chiral supramolecular boron Lewis acid catalysts were prepared from chiral 3-phosphoryl-1,1′-bi-2-naphthols, (2-cyanophenyl)boronic acids, and tris(pentafluorophenyl)borane, bound through CN···B and PO···B coordination bonds. In particular, the coordinated tris(pentafluorophenyl)boranes increase the Lewis acidity of the active center in the manner of a Lewis acid assisted Lewis acid catalyst system. A possible cavity in these catalysts was highly suitable for several Diels–Alder probe reactions of acroleins with cyclic or acyclic dienes, which gave the corresponding adducts in good to high yields and high enantio­selectivities.

Journal

• Synlett

  Synlett 27 (7), 1061-1067, 2016-04

  Georg Thieme Verlag

Keywords

• supramolecular catalysts
• asymmetric catalysis
• Diels–Alder reactions
• Lewis acids
• dienes
• aldehydes

Details

• CRID: 1050845763735803648
• NII Article ID: 120005946823
• DOI: 10.1055/s-0035-1561362
• ISSN: 14372096
• ISSN: 09365214
• HANDLE: 2237/25400
• Web Site: https://nagoya.repo.nii.ac.jp/records/23206
• Web Site: http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0035-1561362.pdf
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN