Fluorinated Aromatic Ketones as Nucleophiles in the Asymmetric Organocatalytic Formation of CC and CN Bonds: A Facile Route to the Construction of Fluorinated Quaternary Stereogenic Centers

• Published in: Chemistry : a European journal Vol. 17; no. 13; pp. 3571 - 3574
• Main Authors: Zhao, Yujun, Pan, Yuanhang, Liu, Hongjun, Yang, Yuanyong, Jiang, Zhiyong, Tan, Choon-Hong
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 21.03.2011; WILEY‐VCH Verlag; Wiley
• Subjects: Amination; Asymmetry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Construction; Fluorination; fluorine; Fluorocarbons; Formations; Guanidines; Halogenation; Hydrocarbons, Fluorinated - chemical synthesis; Hydrocarbons, Fluorinated - chemistry; Ketones; Ketones - chemical synthesis; Ketones - chemistry; Mannich Bases - chemistry; Mannich reaction; Molecular Structure; Nucleophiles; organocatalysis; Physical Sciences; quaternary stereogenic center; Science & Technology; Stereoisomerism; ALPHA,BETA-UNSATURATED KETONES; SUBSTITUTED ALPHA-CYANOACETATES; ALDOL REACTIONS; CYANO KETONES; ENANTIOSELECTIVE MICHAEL ADDITION; organocatalysis; quaternary stereogenic center; BETA-KETOESTERS; Mannich reaction; MANNICH-TYPE REACTIONS; amination; CHIRAL GUANIDINES; fluorine; CONJUGATE ADDITION
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201003761

Highly enantioselective Mannich and α‐amination reactions have been successfully developed using α‐fluorinated aromatic ketones as fluorocarbon nucleophiles in the presence of a bicyclic chiral guanidine (see scheme; Ms=methanesulfonyl). This method is a simple and efficient approach to the construction of fluorinated quaternary stereogenic centers.