Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes

• Kimura, Masanari

• Tamaru, Yoshinao

抄録

Pd-Et3B catalytic system promotes the generation of allyl cations, allyl anions, and zwitterionic trimethylenemethane species from the corresponding allylic alcohols. Allyl cations react with a wide variety of nucleophiles, e.g., amines, active methylene compounds, 1,3,5-trihydroxybenzene, indoles, aldehydes (at the alpha;-position). The reaction is extended to dehydrative Grob fragmentation of 1,3-diols. Allyl anions react with aldimines to give homoallyl amines. Zwitterionic trimethylenemethane, generated from 2-mefhylene-1,3-propanediol, reacts with aldehydes and aldimines to provide 3-methylenecyclopentanols and 3-methylenepyrrolidines, respectively. Vinyl epoxide can be utilized as a synthetic equivalent of 3-butenyl 2-anion-1-cation.

Pure and Applied Chemistry, 80(5), pp.979?991; 2008

収録刊行物

• Pure and Applied Chemistry

  Pure and Applied Chemistry 80 (5), 979-991, 2008-05

  International Union of Pure and Applied Chemistry

キーワード

• allyl alcohols
• allyl cations
• catalysis
• palladium
• triethylborane
• trimethylenemethane
• umpolung
• allyl anions

詳細情報

• CRID: 1050850247227666560
• NII論文ID: 120006981713
• NII書誌ID: AA00797859
• ISSN: 00334545
• HANDLE: 10069/18700
• Web Site: https://nagasaki-u.repo.nii.ac.jp/records/19367
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles
  • KAKEN