Development of the First Spiro Bis(isoxazoline)Ligands (SPRIXs) and Their Applications to Catalytic Enantioselective Reactions

Midori A. Arai, Toshio Shinohara, Takayoshi Aral, Hiroaki Sasai

研究成果: Article査読

4 被引用数 (Scopus)

抄録

The first chiral isoxazoline ligands bearing spiro skeleton are developed. The spiro bis(isoxazoline) ligands (SPRIXs) are readily synthesized from diethyl malonate via double intramolecular nitrile oxide cycloaddition as a key step. The complex of (M, S, S)-R-SPRIX and Pd(OCOCF3)2 promoted the catalytic asymmetric Wacker-type cyclization of alkenyl alcohols to give optically active cyclic ethers for the first time. Furthermore, starting from dialkenyl alcohol, the enantioselective tandem cyclization via oxy-palladation was achieved with up to 95% ee. Asymmetric ligands other than SPRIKs promote neither the Wacker-type reaction nor the tandem reaction.

本文言語English
ページ(範囲)59-69
ページ数11
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
62
1
DOI
出版ステータスPublished - 2004 1月
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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