Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Org Lett. 2010 Jan 15;12(2):260-3. doi: 10.1021/ol9025759.
Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of (E)- and (Z)-allyloxy substituted N-heterocycles generates N-allyl N-heterocyclic amides in good yields and high enantioselectivities (up to 96% ee). The chiral palladacycle COP-Cl (5 mol %) is used as a catalyst with silver(I) trifluoroacetate (10 mol %) at 35-45 degrees C. Examples of heterocycles synthesized include 2-pyridones, quinolin-2(1H)-ones, and isoquinolin-1(2H)-ones.
对映选择性钯（II）催化的（E）-和（Z）-烯丙氧基取代的 N-杂环的形式[3,3]-西格玛重排，以高产率和高对映选择性（高达 96%ee）生成 N-烯丙基 N-杂环酰胺。手性钯环 COP-Cl（5mol%）与三氟乙酸银（10mol%）一起在 35-45℃下用作催化剂。合成的杂环实例包括 2-吡啶酮、喹啉-2(1H)-酮和异喹啉-1(2H)-酮。
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