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Kou, Ying‐Da; Zhao, Zhen‐Ni; Yang, Xing; Kalita, Subarna Jyoti; Chen, Xue‐Jian; Xie, Zhi‐Zhong; Zhao, Yan; Huang, Yi‐Yong
Asian journal of organic chemistry, September 2018, 2018-09-00, 20180901, Letnik: 7, Številka: 9Journal Article
A highly atom‐economic, regio‐ and stereospecific synthesis of fluorinated pyrazolidinones and isoxazolidines is disclosed under catalyst‐ and additive‐free mild conditions. The diastereoselectivity with different type of 1,3‐dipoles is elucidated by using DFT calculations in CH3CN. Furthermore, a reaction using a chiral azomethine imine, a gram‐scale synthesis, and a reductive desulfonylation are also presented. One way or another: A high‐yielding, diastereoselective 1,3‐dipolar cycloaddition of β‐fluoroalkylated unsaturated building blocks providing access to fluoroalkylated heterocycles of pyrazolidinones and isoxazolidines under catalyst‐free conditions is described. The diastereoselective process was supported by DFT calculations.
