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Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition–Wittig olefination†
Chemical Science ( IF 8.4 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1039/c7sc04381c
Kui Zhang 1 , Lingchao Cai 1 , Zhongyue Yang 1 , K N Houk 1 , Ohyun Kwon 1
Affiliation  

A novel bridged [2.2.1] bicyclic phosphine oxide, devised to circumvent the waste generation and burdens of purification that are typical of reactions driven by the generation of phosphine oxides, has been prepared in three steps from commercially available cyclopent-3-ene-1-carboxylic acid. The performance of this novel phosphine oxide was superior to those of current best-in-class counterparts, as verified experimentally through kinetic analysis of its silane-mediated reduction. It has been applied successfully in halide-/base-free catalytic γ-umpolung addition–Wittig olefinations of allenoates and 2-amidobenzaldehydes to produce 1,2-dihydroquinolines with good efficiency. One of the 1,2-dihydroquinoline products was converted to known antitubercular furanoquinolines.

中文翻译:

桥接 [2.2.1] 双环氧化膦促进催化 γ-umpolung 加成——维蒂希烯化†

一种新型桥接 [2.2.1] 双环氧化膦,旨在规避由氧化膦产生驱动的典型反应的废物产生和纯化负担,由市售 cyclopent-3-ene- 分三步制备。 1-羧酸。这种新型氧化膦的性能优于当前同类最佳同类产品,这一点通过对其硅烷介导还原的动力学分析进行了实验验证。它已成功应用于无卤化物/无碱催化 γ-umpolung 加成 - 联烯酸酯和 2-酰胺基苯甲醛的 Wittig 烯化反应,高效生产 1,2-二氢喹啉。一种 1,2-二氢喹啉产品被转化为已知的抗结核呋喃喹啉。
更新日期:2018-01-18
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