High 1,2-Asymmetric Induction in Radical Reactions:Radical Addition to γ-Hydroxy α,β-Unsaturated Carboxylic Esters and Sulfones

• Katsuyuki Ogura

• Akio Kayano

• Motohiro Akazome

書誌事項

タイトル別名

• High 1 2 Asymmetric Induction in Radica

抄録

High 1,2-asymmetric induction was realized by the addition of a 1-hydroxy-1-methylethyl radical to conformationally flexible (E)-γ-hydroxy α,β-unsaturated carboxylic esters and sulfones (1 and 2, respectively). Upon the irradiation (> 290 nm) of (E)-1 and benzophenone in 2-propanol, the 1-hydroxy-1-methylethyl radical was generated in situ and added to (E)-1 with high anti-stereoselectivity. The bulkier is the γ-alkyl group of (E)-1, the higher does the selectivity become. Similarly, a radical addition to the acetates of (E)-1 and (E)-2 proceeded stereoselectively in an anti fashion, whereas (Z)-2 exhibited syn-stereoselectivity. The mechanism for these stereoselective radical additions is discussed.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 70 (12), 3091-3101, 1997-12

  Tokyo : Chemical Society of Japan

キーワード

• General Chemistry

詳細情報

• CRID: 1523669555136387968
• NII論文ID: 10008926763
• NII書誌ID: AA00580132
• ISSN: 00092673
• ISSN: 13480634
• DOI: 10.1246/bcsj.70.3091
• NDL書誌ID: 4371019
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4371019
• Web Site: https://academic.oup.com/bcsj/article-pdf/70/12/3091/56200299/bcsj.70.3091.pdf
• 本文言語コード: en
• NDL 雑誌分類:
  • ZP1(科学技術--化学・化学工業)
• データソース種別:
  • NDL
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  • CiNii Articles