Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3‑Ethynyl-Substituted Tetrahydroquinolines
Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3‑Ethynyl-Substituted Tetrahydroquinolines
复制标题
顺序膦催化 [4 2] β-乙酰氧基联烯酸酯的环化：3-乙炔基取代的四氢喹啉的对映选择性合成
DOI：
10.1021/acs.orglett.9b00130
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
You Huang
中科院分区：
文献类型：
--
作者：
Qinglong Zhang;Hongxing Jin;Jiaxu Feng;Yanna Zhu;Chengzhou Wu;You Huang
本文报道了以乙基取代的全碳四氢喹啉为中心形成四氢喹啉的第一个对映选择性顺序膦催化（简称SPC）模式。在这个SPC过程中，首次设计了一种新的[4 + 2]环化过程，采用α-取代的同位酸盐作为C2合子（α−β′，1,2偶极子）。制备了3-乙基取代四氢喹啉，收率高，对映选择性好。
The first enantioselective sequential phosphine-catalyzed (SPC as abbreviation) mode for the formation of tetrahydroquinolines with an ethynyl-substituted all-carbon quaternary stereogenic center is reported. In this SPC process, a novel [4 + 2] annulation process was devised employing α-substituted allenoates as C2 synthons (α−β′, 1,2-dipole) for the first time. 3-Ethynyl-substituted tetrahydroquinolines were readily prepared in good yields and high enantioselectivities.