Huang Hai, Zhang Tianyu, Sun Jianwei
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, China.
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Angew Chem Int Ed Engl. 2021 Feb 1;60(5):2668-2673. doi: 10.1002/anie.202013062. Epub 2020 Dec 1.
Mild oxetane opening by soft carbon nucleophiles has been developed for efficient C-C bond formation. In the presence of LiNTf or TBSNTf as catalyst, silyl ketene acetals were found to be effective nucleophiles to generate a wide range of highly oxygenated molecules, which are key substructure in natural products like polyketides. Furthermore, intramolecular oxetane opening by a styrene-based carbon nucleophile via a Prins-type process was also achieved with Sc(OTf) as catalyst, leading to efficient formation of the useful 2,3-dihydrobenzo[b]oxepine skeleton.
温和的氧杂环丁烷通过软碳亲核试剂开环已被开发用于高效的C-C键形成。在LiNTf或TBSNTf作为催化剂的存在下，发现甲硅烷基烯酮缩醛是有效的亲核试剂，可生成多种高度氧化的分子，这些分子是聚酮类等天然产物中的关键亚结构。此外，以Sc(OTf)为催化剂，基于苯乙烯的碳亲核试剂通过普林斯型过程实现了分子内氧杂环丁烷的开环，从而高效地形成了有用的2,3-二氢苯并[b]氧杂䓬骨架。
