Petzold Martin, Jones Peter G, Werz Daniel B
Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Angew Chem Int Ed Engl. 2019 May 6;58(19):6225-6229. doi: 10.1002/anie.201814409. Epub 2019 Mar 13.
The first (3+3)-annulation process of donor-acceptor cyclopropanes using synergistic catalysis is reported. The Rh (OAc) -catalyzed decomposition of diazo carbonyl compounds generated carbonyl ylides in situ. These 1,3-dipoles were converted with donor-acceptor cyclopropanes, activated by Lewis acid catalysis, to afford multiply substituted pyran scaffolds in high yield and diastereoselectivity. Extensive optimization studies enabled access to 9-oxabicyclo[3.3.1]nonan-2-one and 10-oxabicyclo[4.3.1]decen-2-ol cores, exploiting solvent effects on intermediate reactivity.
报道了使用协同催化的给体-受体环丙烷的首个(3+3)环化反应过程。Rh(OAc)催化的重氮羰基化合物分解原位生成羰基叶立德。这些1,3-偶极子与经路易斯酸催化活化的给体-受体环丙烷反应，以高产率和非对映选择性得到多取代的吡喃骨架。广泛的优化研究利用溶剂对中间体反应性的影响，得到了9-氧杂双环[3.3.1]壬烷-2-酮和10-氧杂双环[4.3.1]癸烯-2-醇核心结构。
