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Novel Tartrate-Based Guanidines for Enantioselective Fluorination of 1,3-Dicarbonyl and α-Cyano Carbonyl Compounds

Australian Journal of ChemistryPublished 20 May 2014
Li‐Wei Zou, Xiaoze Bao, Huanrui Zhang, Yuming Song, Jingping Qü, Baomin Wang
Citations21
SJR quartileQ3
SJR score0.28
SNIP0.26

Abstract

A novel library of chiral guanidines featuring the tartaric acid skeleton is easily accessed with tunable steric and electronic properties. A guanidine molecule of this library with an incorporated 2,6-diisoaniline fragment was identified as a suitable promoter for the enantioselective fluorination of 1,3-dicarbonyl and α-cyano carbonyl compounds to furnish the fluorinated product with up to 84 % ee and 99 % yield using N-fluorobenzenesulfonimide (NFSI) as the fluorinating agent.

Keywords

ChemistryBiochemistry, Genetics and Molecular BiologyPharmacology, Toxicology and Pharmaceutics