Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole -Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction
Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole -Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction
复制标题
DOI：
10.1002/adsc.201800246
复制
发表时间：
2018-06-05
影响因子：
5.4
通讯作者：
Hashmi, A. Stephen K.
中科院分区：
文献类型：
--
作者：
Nalivela, Kumara Swamy;Rudolph, Matthias;Hashmi, A. Stephen K.
以炔丙基酰胺1和乙醛酸烷基酯3为原料，对映选择性合成恶唑羟基酯衍生物4。一锅法的第一步是选择性分子内原位形成亚烷基恶唑啉2，然后在分子间反应中通过不对称铜（II）催化的Alder-烯反应将其以定量产率和良好至优异的对映选择性对映选择性转化为恶唑-羟基酯衍生物4。
A convenient protocol for the enantioselective synthesis of oxazole -hydroxy ester derivatives 4 from readily available propargylamides 1 and alkylglyoxylates 3 was developed. The first step of the one-pot procedure is the selective intramolecular insitu formation of an alkylideneoxazoline 2, which then in an intermolecular reaction is enantioselectively transformed to the oxazole -hydroxy ester derivatives 4 in quantitative yield and good to excellent enantioselectivity via an asymmetric copper(II)-catalyzed Alder-ene reaction.