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Synthesis of Cyclopropane Fatty Acids by C(sp3)−C(sp3) Cross‐Coupling Reaction and Formal Synthesis of α‐Mycolic Acid
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-08-14 , DOI: 10.1002/adsc.201800901
Takanori Iwasaki 1, 2 , Shohei Terahigashi 1 , Yufei Wang 1 , Arisa Tanaka 1 , Hanqing Zhao 1 , Yukari Fujimoto 3 , Koichi Fukase 4 , Nobuaki Kambe 1
Affiliation  

An iterative Ni‐catalyzed C(sp3)−C(sp3) cross‐coupling reaction of a novel cis‐cyclopropane containing bifunctional building blocks with alkyl halides and alkyl Grignard reagents enabled the introduction of a cyclopropane ring into the desired position(s) of saturated carbon frameworks, providing a straightforward synthetic route to cyclopropane fatty acids. The present method creates a direct route for the construction of saturated carbon frameworks, and can avoid the tedious multistep operations based on unsaturated functional group manipulations that are often employed in conventional synthetic routes. This method could be applicable to the synthesis of trans‐cyclopropane fatty acids and enantioenriched cyclopropane fatty acids. Formal synthesis of α‐mycolic acid was achieved by the C(sp3)−C(sp3) cross‐coupling reaction of cyclopropane‐containing bifunctional building blocks.

中文翻译:

C(sp3)-C(sp3)交叉偶联反应合成环丙烷脂肪酸及α-霉菌酸的形式合成

新型的含双功能结构单元的顺式-环丙烷与烷基卤化物和烷基格氏试剂的Ni迭代催化C(sp 3)-C(sp 3)交叉偶联反应可将环丙烷环引入所需位置)的饱和碳骨架,提供了直接合成环丙烷脂肪酸的途径。本方法创建了用于构建饱和碳骨架的直接途径,并且可以避免基于在常规合成途径中经常采用的不饱和官能团操纵的繁琐的多步操作。该方法可适用于反式的合成-环丙烷脂肪酸和对映体富集的环丙烷脂肪酸。含环丙烷的双功能结构单元的C(sp 3)-C(sp 3)交叉偶联反应实现了α-霉菌酸的正式合成。
更新日期:2018-08-14
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