Kyoto Pharmaceutical University, Yamashina, Kyoto, 607-8412, Japan.
Org Lett. 2011 May 6;13(9):2350-3. doi: 10.1021/ol2005984. Epub 2011 Apr 1.
A Pd(II)-catalyzed cascade reaction of chiral nonracemic allylic alcohols possessing an internal mono- or diepoxide and a terminal alcohol provided a contiguous THF-THF ring unit stereospecifically. The cyclization takes place in a 5-exo-tet-5-exo-trig fashion with high chirality transfer through a syn-S(N)2' like process for the formation of the internal THF ring. Chiral bis- and tris-THF-THF ring units were effectively prepared from acyclic precursors by the Pd-catalyzed reaction.
Pd(II)催化的手性非外消旋烯丙醇的级联反应，具有内部单环氧化物或二环氧化物和末端醇，立体特异性地提供了连续的四氢呋喃-四氢呋喃环单元。环化以 5-exo-tet-5-exo-trig 方式发生，通过类似 syn-S(N)2'的过程进行高手性转移，形成内部四氢呋喃环。手性双和三-四氢呋喃-四氢呋喃环单元可以通过 Pd 催化反应从无环前体有效制备。
