Heterocycle Synthesis via Radical Addition-Cyclization of Oxime Ethers.

• Miyabe Hideto

  Kobe Pharmaceutical University

• Miyata Okiko

  Kobe Pharmaceutical University

• Naito Takeaki

  Kobe Pharmaceutical University

Abstract

Oxime ethers connected by a tether to aldehydes or ketones efficiently cyclized via stannyl radical addition-cyclization to give a new entry to heterocyclic amino alcohols. The SmI₂-induced radical cyclization was found to be effective for preparing cyclic trans-amino alcohols. These radical reactions provide a novel method for the synthesis of (-) -balanol, aminocyclitols, 1-deoxynojirimycin, 2-substituted 5-amino-4-piperidinol, and nucleoside analogs. The sulfanyl radical addition-cyclization-elimination reaction was developed, which was successfully applied to the synthesis of (-) -kainic acid. The sulfanyl radical addition-cyclization of oxime ethers gave a method for synthesis of rigidified cyclic β-amino acids. The carbon radical addition-cyclization reaction of substrates having two different radical acceptors such as acrylate and aldoxime ether moieties proceeded even in aqueous media via a diastereoselective tandem C-C bond-forming process, providing a method for asymmetric synthesis of γ-butyrolactones and γ-amino acids.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 60 (11), 1087-1094, 2002

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• Organic Chemistry

Details

• CRID: 1390001205277868544
• NII Article ID: 10012595076
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.60.1087
• COI: 1:CAS:528:DC%2BD38XoslOitbc%3D
• ISSN: 18836526
• ISSN: 00379980
• ISSN: http://id.crossref.org/issn/00379980
• NDL BIB ID: 6351150
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6351150
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed