2価のパラジウム触媒を用いる含窒素ヘテロ環の立体選択的な構築と天然物不斉合成への応用

Yoshiro Hirai*, Hajime Yokoyama

*この論文の責任著者

研究成果: ジャーナルへの寄稿総説査読

5 被引用数 (Scopus)

抄録

Stereoselective amino-cycloaddition of alkenylamines is one of the most important approaches for the stereoselective construction of nitrogen hetero-alicycles, which form the skeletons of several biologically active natural products and related compounds. We recently developed the intramolecular substitution of an allylic alcohol by a heteroatom using a palladium (II) catalyst without activation of the allylic alcohol. This review describes the stereoselective cyclization of the optically active urethanes and oxazolidinones containing allyl alcohol moiety using bis(acetonitrile)palladium(II) chloride leading to the 2-functionalized 5-hydroxypiperidine, the trans-2,5-disubstituted pyrrolidine, and the trans -2,6-piperidine, respectively. The stereoselective construction of different stereoisomers from similar precursors by changing transition metals (a palladium(II) catalyst → a silver salt) is also described. The cyclo-adducts obtained were proved to be useful chiral building blocks by their conversion into (+)-coniine, (-)-5-hydroxysedamine, (-)-bulgecinine, (+)-prosopinine, and a prospective synthetic intermediate of (+)-palustrine, respectively.

寄稿の翻訳タイトルPalladium(II)-catalyzed cyclization via N-alkylation of an allyl alcohol by a urethane and its application to the syntheses of natural products
本文言語日本
ページ(範囲)34-44
ページ数11
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
56
1
DOI
出版ステータス出版済み - 1998/01

ASJC Scopus 主題領域

  • 有機化学
  • 生化学
  • 創薬
  • 化学一般

引用スタイル