Novel Tartrate-Based Guanidines for Enantioselective Fluorination of 1,3-Dicarbonyl and α-Cyano Carbonyl Compounds
Liwei Zou A , Xiaoze Bao A , Huanrui Zhang A , Yuming Song A , Jingping Qu A and Baomin Wang A B
+ Author Affiliations
- Author Affiliations
A State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, China.
B Corresponding author. Email: bmwang@dlut.edu.cn
Australian Journal of Chemistry 67(7) 1115-1118 https://doi.org/10.1071/CH14179
Submitted: 31 March 2014 Accepted: 28 April 2014 Published: 21 May 2014
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.
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