N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimine: Versatile Reagent for Asymmetric Synthesis of Trifluoromethyl-Containing Amines and Amino Acids of Pharmaceutical Importance

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• 作者：Haibo Mei ; Chen Xie ; Jianlin Han and Vadim A. Soloshonok
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：December 2016
• 年：2016
• 卷：2016
• 期：36
• 页码：5917-5932
• 全文大小：2517K
• ISSN：1099-0690

文摘

Synthetic methods for the preparation of compounds containing trifluoromethyl groups are in extremely high demand in nearly every sector of the chemical industry. Over the last several years the chemistry of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine has undergone particular development. Currently, it is commonly used as a versatile reagent for general asymmetric synthesis of trifluoromethyl-containing amines and amino acids of pharmaceutical potential. This review provides a critical and comprehensive overview of synthetic applications of this reagent as well as of several relevant analogues, such as aldimines containing –CHF₂, –CClF₂, –CBrF₂, and –CF₂P(O)(OEt)₂ groups and N-tert-butylsulfinyl-3,3,3-trifluoromethyl-substituted ketimines. Where it is possible, we emphasize the structural novelty and pharmaceutic value of the products obtainable by application of these reagents.