高非对映选择性钯催化的非环内烯烃的碳醚化反应。多取代四氢呋喃的立体选择性合成。
Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.
机构信息
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
出版信息
Org Lett. 2010 Mar 19;12(6):1268-71. doi: 10.1021/ol1001472.
Abstract
A highly diastereoselective synthesis of substituted tetrahydrofurans bearing stereocenters at C2 and C1' via Pd-catalyzed carboetherification reactions of acyclic internal alkenes is described. Use of an improved catalyst composed of Pd(2)(dba)(3)/S-Phos provides products with up to >20:1 dr. The stereoselective preparation of tetrahydrofurans containing three stereocenters, including a molecule structurally related to simplakidine A, is also reported.
摘要
通过非环内部烯烃的 Pd 催化碳醚化反应，高非对映选择性地合成了在 C2 和 C1'位具有手性中心的取代四氢呋喃。使用由 Pd(2)(dba)(3)/S-Phos 组成的改进催化剂，可以得到高达>20:1 dr 的产物。还报道了包含三个手性中心的四氢呋喃的立体选择性制备，包括与 simplakidine A 结构相关的分子。
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