Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, 91198 Gif-sur-Yvette (France).
Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5470-3. doi: 10.1002/anie.201500299. Epub 2015 Mar 5.
The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene- or alkylidenemalononitriles and γ-substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.
首次报道了膦薁在对映选择性有机催化中的应用。新的手性膦薁已被制备,并能够实现芳基亚甲基-或烷基亚甲基马来腈与γ-取代的烯丙基酯或氰基烯与之间的高对映选择性[3+2]环化反应。这些反应以高收率和非对映选择性提供环戊烯衍生物,对映过量最高可达 97%。