Practical Synthesis of 4,4,4-Trifluorocrotonaldehyde: A Versatile Precursor for the Enantioselective Formation of Trifluoromethylated Stereogenic Centers via Organocatalytic 1,4-Additions
Practical Synthesis of 4,4,4-Trifluorocrotonaldehyde: A Versatile Precursor for the Enantioselective Formation of Trifluoromethylated Stereogenic Centers via Organocatalytic 1,4-Additions
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4,4,4-三氟巴豆醛的实际合成：通过有机催化 1,4-加成对映选择性形成三氟甲基化立体中心的多功能前体
DOI：
10.1039/c2cc32757k
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发表时间：
2012
影响因子：
4.9
通讯作者：
Seiji Iwasa
中科院分区：
文献类型：
--
作者：
Kazutaka Shibatomi;Akira Narayama;Yoshiyuki Abe;Seiji Iwasa
介绍了4，4，4-三氟巴豆醛（1）的合成及其在对映选择性1，4-加成反应中的应用。1与几种亲核试剂如杂芳族化合物、烷基硫醇和醛肟的有机催化1，4-加成得到相应的产物，每种产物都带有高光学纯度的三氟甲基化立体异构中心。将所得产物转化为MAO-A抑制剂贝伐他汀。
The practical synthesis of 4,4,4-trifluorocrotonaldehyde (1) and its application to enantioselective 1,4-additions are described. The organocatalytic 1,4-addition of 1 with several nucleophiles such as heteroaromatics, alkylthiols and aldoximes afforded the corresponding products, each bearing a trifluoromethylated stereogenic center with high optical purity. A resulting product was converted into an MAO-A inhibitor, befloxatone.