对映选择性金（I）催化的炔丙基-烯酰胺水合环化反应生成3,6-二氢吡啶酮
Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of -Propargyl-ynamides into 3,6-Dihydropyridinones.
作者信息
Febvay Julie, Sanogo Youssouf, Retailleau Pascal, Gogoi Manash Protim, Sahoo Akhila K, Marinetti Angela, Voituriez Arnaud
机构信息
Institut de Chimie des Substances Naturelles , CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay , 1 av. de la Terrasse , 91198 Gif-sur-Yvette , France.
School of Chemistry , University of Hyderabad , Hyderabad 500046 , India.
出版信息
Org Lett. 2019 Dec 6;21(23):9281-9285. doi: 10.1021/acs.orglett.9b02644. Epub 2019 Nov 25.
This study discloses the first enantioselective variant of the gold(I)-catalyzed hydrative cyclizations of ynamides, which have been implemented by using bis-gold(I) complexes of chiral diphosphines. Starting from -propargyl-ynamides and water in the presence of -toluenesulfonic acid, the cyclization reactions afford -tosyl-3,6-dihydropyridin-2(1)-ones in good isolated yields and with high levels of stereocontrol (20 examples, enantiomeric ratios up to 94:6).
本研究揭示了金（I）催化的烯酰胺水合环化反应的首例对映选择性变体，该反应通过使用手性二膦的双金（I）配合物来实现。从α-炔丙基烯酰胺和水出发，在对甲苯磺酸存在下进行环化反应，可得到α-甲苯磺酰基-3,6-二氢吡啶-2(1)-酮，分离产率良好且具有高度的立体控制（20个实例，对映体比例高达94:6）。
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