Mn(III)‐Based Oxidative Cyclization of Alkenes Using Tricarbonyl System

• 西野, 宏

• Huynh, Thanh-Truc

• Yamakawa, Hiroyasu

• Nguyen, Van-Ha

抄録

The Mn(III)‐based oxidation of 1,1‐disubstituted ethenes with 2‐(2‐aryl‐2‐oxoethyl)malonates, 2‐acetyl‐4‐aryl‐4‐oxobutanoates, and 3‐acetyl‐1‐arylpentane‐1,4‐diones was evaluated. The reaction using the malonates mainly gave the 2,3‐dihydro‐4 H ‐pyran‐4,4‐dicarboxylates along with γ ‐lactones. A similar reaction using the acetyloxobutanoates and acetylpentanediones produced the 2,3,3a,6a‐tetrahydrofuro[2, 3‐ b ]furans and the corresponding dihydropyrans. The cyclization was strongly affected by the nucleophilicity of the carbonyl oxygen in the carbocation intermediate, and the kinetic and thermodynamic controls of the following reaction. The structure determination and the mechanisms are discussed.

収録刊行物

• ChemistrySelect

  ChemistrySelect 3 (23), 6414-6420, 2018-06-19

  Wiley‐VCH

キーワード

• 2-Acetyl-4-aryl-4-oxobutanoates
• 3-Acetyl-1-arylpentane-1,4-diones
• 2-(2-Aryl-2-oxoethyl)malonates
• Dihydro-2H-pyrans
• 5-endo-trig
• 6-endo-trig
• Manganese(III) acetate
• Oxidative cyclization
• Tandem cyclization
• 2,3,3a,6a-Tetrahydrofuro[2,3-b]furans

詳細情報

• CRID: 1050565163714169088
• NII論文ID: 120006786275
• DOI: 10.1002/slct.201801443
• HANDLE: 2298/43170
• ISSN: 23656549
• Web Site: https://kumadai.repo.nii.ac.jp/records/30977
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fslct.201801443
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/slct.201801443
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.201801443
• 本文言語コード: en
• 資料種別: article
• データソース種別:
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