Asymmetric Synthesis of Sterically and Electronically Demanding Linear 蠅-Trifluoromethyl Containing Amino Acids via Alkylation of Chiral Equivalents of Nucleophilic Glycine and Alanine

详细信息    查看全文

• 作者：Jiang Wang ; Daizong Lin ; Shengbin Zhou ; Xiao Ding ; Vadim A. Soloshonok ; Hong Liu
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：January 21, 2011
• 年：2011
• 卷：76
• 期：2
• 页码：684-687
• 全文大小：779K
• 年卷期：v.76,no.2(January 21, 2011)
• ISSN：1520-6904

文摘

An operationally convenient, scalable asymmetric synthesis of linear, 蠅-trifluoromethyl-containing amino acids, which were not previously produced in their enantiomerically pure form, has been developed via alkylation of chiral equivalents of nucleophilic glycine and alanine. The simplicity of the experimental procedures and high stereochemical outcome (yields up to 90% and diastereoselectivity up to 99%) of the presented method render these fluorinated amino acids readily available for systematic medicinal chemistry studies and de novo peptide design.