Kawamura Yasufumi, Kawano Yasuhiro, Matsuda Tomohiro, Ishitobi Yûta, Hosokawa Takahiro
Department of Environmental Systems Engineering, Kochi University of Technology, 185 Miyanokuchi, Tosayamada, Kami-City, Kochi 782-8502, Japan.
J Org Chem. 2009 Apr 17;74(8):3048-53. doi: 10.1021/jo802807w.
The use of PdX(2), CuX(2) (X = OAc, OCOCF(3), or Cl), and catechol together with (S,S)-4,4'-bisbenzyl-2,2'-bioxazoline under O(2) induces the asymmetric coupling of cinnamyl alcohols and vinyl ethers to give (R)-(+)-2-alkoxy-4-benzylidenetetrahydrofurans in 40-53% ee (79% yield). The present study provides implications for the so-called Wacker catalyst of PdX(2) and CuX(2), in terms of that the anionic ligands (X) of Pd and Cu interchange between two metals.
在氧气存在下,将PdX₂、CuX₂(X = OAc、OCOCF₃或Cl)与邻苯二酚以及(S,S)-4,4'-双苄基-2,2'-二恶唑啉一起使用,可诱导肉桂醇和乙烯基醚发生不对称偶联,生成对映体过量值为40 - 53%(产率79%)的(R)-(+)-2-烷氧基-4-亚苄基四氢呋喃。本研究就PdX₂和CuX₂所谓的瓦克催化剂而言提供了启示,即Pd和Cu的阴离子配体(X)在两种金属之间发生交换。