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- W2950161337 abstract "Chiral homoallylic amines not only are found in pharmaceutically relevant compounds but also serve as versatile building blocks for chemical synthesis. However, catalytic allylation of ketimines with allylboronates, an attractive approach to synthesize chiral homoallylic amine scaffolds remain scarce. Herein, we develop a highly enantioselective allylation of isatin-derived ketimines with boron allylation reagents catalyzed by a Bi(OAc)3-chiral phosphoric acid catalyst system. The reactions are remarkably efficient and mild, most of which were completed in less than an hour at room temperature with only 1/2 mol% (Bi(OAc)3/CPA) catalyst loading. A wide range of chiral 3-allyl 3-aminooxindoles were obtained in excellent yields and enantioselectivities. The synthetic utility was demonstrated by efficient formal synthesis of (+)-AG-041R and (−)-psychotriasine. Preliminary mechanism was studied by control experiments and theoretical calculations." @default.
- W2950161337 created "2019-06-27" @default.
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- W2950161337 date "2019-06-01" @default.
- W2950161337 modified "2023-09-24" @default.
- W2950161337 title "Bi(III)-Catalyzed Enantioselective Allylation Reactions of Ketimines" @default.
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- W2950161337 doi "https://doi.org/10.1016/j.isci.2019.06.006" @default.
- W2950161337 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6593186" @default.
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