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- W2341497013 abstract "The combination of amide activation by Tf2O with B(C6F5)3-catalyzed hydrosilylation with TMDS constitutes a method for the one-pot reduction of secondary amides to amines under mild conditions. The method displays a broad applicability for the reduction of many types of substrates, and shows good compatibility and excellent chemoselectivity for many sensitive functional groups. Reductions of a multifunctionalized α,β-unsaturated amide obtained from another synthetic methodology, and a C–H functionalization product produced the corresponding amines in good to excellent yield. Chemoselective reduction of enantiomeric pure (ee >99%) tetrahydro-5-oxo-2-furaneamides yielded 5-(aminomethyl)dihydrofuran-2(3H)-ones in a racemization-free manner. The latter were converted in one pot to N-protected 5-hydroxypiperidin-2-ones, which are building blocks for the synthesis of many natural products. Further elaboration of an intermediate led to a concise four-step synthesis of (−)-epi-pseudoconhydrine." @default.
- W2341497013 created "2016-06-24" @default.
- W2341497013 creator A5015452019 @default.
- W2341497013 creator A5048553281 @default.
- W2341497013 creator A5084356579 @default.
- W2341497013 date "2016-05-04" @default.
- W2341497013 modified "2023-09-30" @default.
- W2341497013 title "Mild Metal-Free Hydrosilylation of Secondary Amides to Amines" @default.
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- W2341497013 doi "https://doi.org/10.1021/acs.joc.6b00572" @default.
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