著者

荒井 緑 篠原 俊夫 荒井 孝義 笹井 宏明

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.1, pp.59-69, 2004-01-01

被引用文献数

5

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The first chiral isoxazoline ligands bearing spiro skeleton are developed. The spiro bis (isoxazoline) ligands (SPRIXs) are readily synthesized from diethyl malonate <I>via</I> double intramolecular nitrile oxide cycloaddition as a key step. The complex of (<I>M, S, S</I>) -R-SPRIX and Pd (OCOCF<SUB>3</SUB>)<SUB>2</SUB> 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 <I>via</I> oxy-palladation was achieved with up to 95% ee. Asymmetric ligands other than SPRIXs promote neither the Wacker-type reaction nor the tandem reaction.