Asymmetric Synthesis of Fused Bicyclic N,O- and O,O-Acetals via Cascade Reaction by Gold(I)/N,N'-Dioxide-Nickel(II) Bimetallic Relay Catalysis
Asymmetric Synthesis of Fused Bicyclic N,O- and O,O-Acetals via Cascade Reaction by Gold(I)/N,N'-Dioxide-Nickel(II) Bimetallic Relay Catalysis
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DOI：
10.1002/adsc.201800576
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发表时间：
2018-08-06
影响因子：
5.4
通讯作者：
Feng, Xiaoming
中科院分区：
文献类型：
--
作者：
Hu, Bowen;Li, Jun;Feng, Xiaoming
研究了β，γ-不饱和α-酮酯与烷基酰胺或醇的催化不对称环化/反电子需Hetero-Diels-桤木级联反应。该方法是基于使用手性金（I）催化剂和手性N，N '-二氧化物/Ni（II）催化剂的双金属催化剂体系，在温和的反应条件下以高达99%的产率和99%ee（>19：1 dr）提供各种稠合双环N，O-缩醛或O，O-缩醛。在对照实验和前人研究的基础上，提出了一种可能的间歇催化级联反应途径。
An efficient catalytic asymmetric cyclization/inverse-electron-demand hetero-Diels-Alder cascade reaction of beta,gamma-unsaturated alpha-ketoesters with alkyl amides or alcohols were accomplished. The process was based on the utilization bimetallic catalyst system with achiral gold(I) catalyst and chiral N,N'-dioxide/Ni(II) catalyst, delivering a variety of fused bicyclic N,O-acetals or O,O-acetals in up to 99% yield and 99% ee with >19:1 dr under mild reaction conditions. Based on the control experiments and previous studies, a possible reaction pathway of bimetallic relay catalysis cascade reactions was presented.