Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.
Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.
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DOI：
10.1002/anie.201408928
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发表时间：
2014-12-15
期刊：
影响因子：
--
通讯作者：
Bull JA
中科院分区：
文献类型：
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作者：
Davis OA;Bull JA
氧杂环丁烷在药物发现和材料科学中作为结构基序和中间体提供了令人兴奋的潜力。在这里，氧杂环丁烷环纳入侧官能团的合成的有效策略进行了描述。以高产率获得各种各样的氧杂环丁烷2，2_二羧酸酯，包括官能化的3-/4-芳基-和烷基-取代的氧杂环丁烷和稠合氧杂环丁烷双环。对映体富集的醇提供了对映体富集的氧杂环丁烷，其构型完全保留。氧杂环丁烷产物被进一步衍生化，而环保持完整，从而突出了它们作为药物化学结构单元的潜力。
Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl- and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.