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

作者：Hu, Bowen; Li, Jun; Cao, Weidi; Lin, Qianchi; Yang, Jian; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming^*

来源：Advanced Synthesis & Catalysis, 2018, 360(15): 2831-2835.

DOI：10.1002/adsc.201800576

• asymmetric relay catalysis
• gold
• nickel
• cycloaddition
• fused bicyclic heterocycles

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.

• 出版日期2018-8-6
• 单位四川大学