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Published on: May 21, 2019
Highly Enantioselective α-Cyanation with 4-Acetylphenyl Cyanate
Jia-Shen Qiu1, Yao-Feng Wang1, Gui-Rong Qi1
1School of Chemical Engineering and the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian district, Beijing, 100081, P. R. China.
Abstract:
A highly effective asymmetric version of α-cyanation of β-keto esters and amides was developed with a Lewis-acid catalyst. Thus, by using 10 mol % of a tridentate bisoxazoline-zinc(II) complex as the catalyst, a series of chiral nitriles containing a quaternary carbon center were obtained in excellent enantioselectivities (up to 97 % enantiomeric excess) and up to 95 % yield in the presence of 4 Å molar sieve at room temperature. For the first time, mild and active 4-acetylphenyl cyanate was used instead of cyano-hyperiodinate as the cationic cyano source for catalytic asymmetric α-cyanation.
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