Battula Shravani, Kothuri Pranay, Bhumannagari Haripriya, Nayani Kiranmai
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Org Biomol Chem. 2024 Feb 21;22(8):1671-1675. doi: 10.1039/d3ob01893h.
The development of efficient and straightforward strategies for obtaining chiral complex molecules from readily available starting materials is of great value in drug discovery. The stereodivergent synthesis of heterocycles bearing quaternary centers remains a challenge due to inherent steric issues. Herein, we report an enantioselective copper-catalyzed decarboxylative [3 + 2] cycloaddition of propargyl cyclic carbonates/carbamates with 4-hydroxycoumarins to afford a wide range of dihydrofuro[3,2-]coumarins in excellent yields and enantioselectivity. The strategy has been successfully applied to other ,-bisnucleophiles, such as α-naphthols, to obtain dihydronaphtho[1,2-]furans with good yields.
从易得的起始原料开发高效且直接的策略来获取手性复杂分子在药物发现中具有重要价值。由于固有的空间问题，含有季碳中心的杂环的立体发散合成仍然是一个挑战。在此，我们报道了一种对映选择性铜催化的炔丙基环状碳酸酯/氨基甲酸酯与4-羟基香豆素的脱羧[3 + 2]环加成反应，以优异的产率和对映选择性得到了一系列二氢呋喃并[3,2 - ]香豆素。该策略已成功应用于其他α,β-双亲核试剂，如α-萘酚，以良好的产率得到二氢萘并[1,2 - ]呋喃。
