- 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
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.