Highly enantioselective conjugate addition of cyclic diketones to β,γ-unsaturated α-Ketoesters catalyzed by an N,N′-dioxide-Cu(OTf)2 complex

Dong Z.; Feng J.; Fu X.; Liu X.; Lin L.; Feng X.

首页> 外文期刊>Chemistry: A European journal >Highly enantioselective conjugate addition of cyclic diketones to β,γ-unsaturated α-Ketoesters catalyzed by an N,N′-dioxide-Cu(OTf)2 complex

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Highly enantioselective conjugate addition of cyclic diketones to β,γ-unsaturated α-Ketoesters catalyzed by an N,N′-dioxide-Cu(OTf)2 complex

机译：N，N'-二氧化物-Cu（OTf）2配合物催化的环状对酮向β，γ-不饱和α-酮酸酯的高度对映选择性共轭加成

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Copper-catalyzed conjugate addition: A highly enantioselective conjugate addition of cyclic diketones to β,γ-unsaturated α-ketoesters was achieved by using a two-carbon-linked N,N′-dioxide-Cu(OTf)2 complex. Excellent yields (up to 99%) and enantioselectivities (up to 99% ee) were obtained with 2 mol% catalyst loading (see scheme). By using this method, adducts could be easily transformed into hexahydroquinolines. The reaction could also be scaled-up to gram quantities without any loss in yield or enantioselectivity.

机译：铜催化的共轭物加成：通过使用两个碳连接的N，N'-二氧化物-Cu（OTf）2络合物，可以将环状二酮高度对映选择性地共轭添加到β，γ-不饱和的α-酮酸酯中。在催化剂负载量为2 mol％的情况下，可获得极佳的收率（高达99％）和对映选择性（高达99％ee）（请参见方案）。通过使用这种方法，加合物可以轻松地转化为六氢喹啉。反应也可以按比例放大至克量，而没有产率或对映选择性的任何损失。

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《Chemistry: A European journal》 |2011年第4期|共4页
作者
Dong Z.; Feng J.; Fu X.; Liu X.; Lin L.; Feng X.;
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正文语种 eng
中图分类应用化学;
关键词
asymmetric catalysis; copper; hexahydroquinoline; ketoesters; Michael addition;

机译：不对称催化;铜;六氢喹啉;酮酸酯;迈克尔加成;

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1. Highly enantioselective conjugate addition of cyclic diketones to β,γ-unsaturated α-Ketoesters catalyzed by an N,N′-dioxide-Cu(OTf)2 complex [J] . Dong Z., Feng J., Fu X., Chemistry: A European journal . 2011,第4期

机译：N，N'-二氧化物-Cu（OTf）2配合物催化的环状对酮向β，γ-不饱和α-酮酸酯的高度对映选择性共轭加成
2. Asymmetric Cycloaddition of β,-Unsaturated -Ketoesters with Electron-Rich Alkenes Catalyzed by a Chiral Er(OTf)₃/N,N′-Dioxide Complex: Highly Enantioselective Synthesis of 3,4-Dihydro-2?H-pyrans? [J] . Yin Zhu Mingsheng Xie Shunxi Dong Xiaohu Zhao Dr. Lili Lin Dr. Xiaohua Liu Prof. Dr. Xiaoming Feng Chemistry - A European Journal . 2011,第29期

机译：手性Er（OTf）_{3 / N，N'-二氧化物配合物催化β-不饱和酮酸酯与电子丰富的烯烃的不对称环加成反应：3,4-二氢-2的高对映选择性合成？H-pyrans ？}
3. Asymmetric cycloaddition of β,γ-unsaturated α-ketoesters with electron-rich alkenes catalyzed by a chiral Er(OTf)_3/N,N'- dioxide complex: Highly enantioselective synthesis of 3,4-dihydro-2H-pyrans [J] . Zhu Y., Xie M., Dong S., Chemistry: A European journal . 2011,第29期

机译：β（γ）-不饱和α-酮酸酯与手性Er（OTf）_3 / N，N'-二氧化物配合物催化的富电子烯烃的不对称环加成反应：3,4-二氢-2H-吡喃的高对映选择性合成
4. Chiral Rhodium Nanoparticle Catalyzed Asymmetric 1,4-Addition of Aryl Boronic Acids to β,γ-Unsaturated-α-ketoesters [C] . Hiroyuki MIYAMURA, Shu KOBAYASHI 日本化学会春季年会講演予稿集 . 2018

机译：手性铑纳米粒子催化不对称1,4-加入芳基硼酸至β，γ-不饱和-α-酮甾体
5. Copper-catalyzed enantioselective conjugate additions of organometal reagents to unsaturated carbonyls: An enantioselective total synthesis of clavirolide C [D] . Brown, Michael Kevin 2008

机译：铜催化的有机金属试剂对不饱和羰基化合物的对映选择性共轭加成：克拉维洛利C的对映选择性全合成
6. Enantioselective Conjugate Silyl Additions to Cyclic and Acyclic Unsaturated Carbonyls Catalyzed by Cu Complexes of Chiral N-Heterocyclic Carbenes [O] . Kang-sang Lee, Amir H. Hoveyda -1

机译：对映选择性共轭甲硅烷添置环状和无环不饱和羰基化合物催化手性N-杂环卡宾的铜配合物
7. Highly enantioselective copper-catalyzed 1,4-conjugate addition of diethylzinc to cyclic enones and α,β-unsaturated lactones [O] . Liang L, Yan M, Li YM, 2004

机译：高对映选择性铜催化的二乙基锌向环烯酮和α，β-不饱和内酯的1,4-共轭加成

Highly enantioselective conjugate addition of cyclic diketones to β,γ-unsaturated α-Ketoesters catalyzed by an N,N′-dioxide-Cu(OTf)2 complex

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