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- Title
Highly Enantioselective α-Cyanation with 4-Acetylphenyl Cyanate.
- Authors
Qiu, Jia ‐ Shen; Wang, Yao ‐ Feng; Qi, Gui ‐ Rong; Karmaker, Pran G.; Yin, Hong ‐ Quan; Chen, Fu ‐ Xue
- 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.
- Subjects
CYANATES; ASYMMETRIC synthesis; KETONIC acids; LEWIS acidity; NITRILE synthesis; LEWIS acids
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 8, p1775
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201605610