Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland.
Org Lett. 2015 Apr 17;17(8):1890-3. doi: 10.1021/acs.orglett.5b00571. Epub 2015 Mar 31.
A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp(3))-O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted epoxides via formation of a C(sp(3))-C(sp(3)) and a C(sp(3))-O bond with moderate to excellent diastereoselectivity.
发展了一种铜催化的烯丙醇的氧烷基化反应，使用非活化的烷基腈作为反应伙伴。提出了一个反应历程，包括烷基腈自由基的生成，然后加成到双键上，以及铜介导的 C(sp(3))-O 键形成，以解释反应结果。该方案通过形成 C(sp(3))-C(sp(3))和 C(sp(3))-O 键，提供了一种高效的合成功能化的三取代和四取代环氧化合物的途径，具有中等至优异的非对映选择性。
