Highly Enantioselective α-Cyanation with 4-Acetylphenyl Cyanate
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- 作者：Jia-Shen Qiu ; Yao-Feng Wang ; Gui-Rong Qi ; Pran G. Karmaker ; Dr. Hong-Quan Yin and Prof. Dr. Fu-Xue Chen
- 刊名：Chemistry - A European Journal
- 出版年：2017
- 出版时间：February 3, 2017
- 年：2017
- 卷：23
- 期：8
- 页码：1775-1778
- 全文大小：2048K
- ISSN：1521-3765
文摘
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.