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- Title
Enantioselective Fluorination of β-Ketoamides Catalyzed by Ar-BINMOL-derived SalanCopper Complex.
- Authors
Zheng, Long ‐ Sheng; Wei, Yun ‐ Long; Jiang, Ke ‐ Zhi; Deng, Yuan; Zheng, Zhan ‐ Jiang; Xu, Li ‐ Wen
- Abstract
A facile and powerful enantioselective construction of CF containing molecules was successfully developed through asymmetric fluorination of β-ketoamides catalyzed by Ar-BINMOL-derived salan-CuII system (Ar-BINMOL=1,1′-Binaphthalene-2-α-arylmethanol-2′-ol, Cu = copper). The present catalytic system exhibited excellent enantioselectivity and a broad substrate scope for indanone-derived β-ketoamides under mild conditions (up to 99 % ee and 99 % yields). Notably, the biomimetic salan-copper complex was demonstrated for the first time to be a highly efficient catalyst in the fluorination of β-ketoamides. Experimental results and mechanistic studies indicated that both excess amount of copper salt and electrophilic attack of cationic fluorine to activated methylene assisted by amide group on the β-ketoamides were key factors for high yield and excellent enantioselectivity, respectively, in this enantioselective fluorination, which was controlled by the two-point binding between the salan-copper complex with cyclic β-ketoamides and hydrogen-bonding activation of the electrophilic fluorinating reagent.
- Subjects
AMIDES; FLUORINE; HYDROGEN bonding; ORGANIC compounds; HALOGENS
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 18, p3769
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201400603