Diastereoselective Synthesis and Conformational Analysis of (2R)- and (2S)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde

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• 作者：Xiang-Guo Hu ; Aggie Lawer ; Matthew B. Peterson ; Hasti Iranmanesh ; Graham E. Ball ; Luke Hunter
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：18
• 期：4
• 页码：662-665
• 全文大小：320K
• ISSN：1523-7052

文摘

Stereoselectively fluorinated analogues of the amino acid statine have been efficiently synthesized. The key step is an organocatalytic electrophilic fluorination of a chiral β-oxygenated aldehyde, which provided a test of both diastereoselectivity and chemoselectivity. The target statine analogues were found to adopt unique conformations influenced by the fluorine gauche effect, rendering them potentially valuable building blocks for incorporation into bioactive peptides.