Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles
Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles
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将羰基烯烃复分解方法的保护基范围扩大到 2,5-二氢吡咯
DOI：
10.1021/acs.joc.1c02447
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Tiefenbacher Konrad
中科院分区：
文献类型：
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作者：
Huck Fabian;Catti Lorenzo;Reber Gian Lino;Tiefenbacher Konrad
手性吡咯烷衍生物是天然产物合成的重要结构单元。羰基烯烃复分解反应最近已经成为从手性氨基酸衍生物构建这种结构单元的有力工具。在这里，我们证明了超分子间苯二酚芳烃催化剂能够在布朗斯台德酸催化下获得手性2，5-二氢吡咯。此外，该催化体系甚至耐受与替代催化剂不相容的路易斯碱性保护基团如甲磺酸酯。正如对于封闭腔内的转化所预期的，产物产率和选择性取决于底物的大小。
Chiral pyrrolidine derivatives are important building blocks for natural product synthesis. Carbonyl olefin metathesis has recently emerged as a powerful tool for the construction of such building blocks from chiral amino acid derivatives. Here, we demonstrate that the supramolecular resorcinarene catalyst enables access to chiral 2,5-dihydropyrroles under Brønsted acid catalysis. Moreover, this catalytic system even tolerated Lewis-basic-protecting groups like mesylates that are not compatible with alternative catalysts. As expected for conversion inside a closed cavity, the product yield and selectivity depended on the size of the substrates.