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. Issue 15 (17th June 2018)

• Record Type: Journal Article
• Authors: Hu, Bowen; Li, Jun; Cao, Weidi; Lin, Qianchi; Yang, Jian; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 15(2018)
• Page Start: 2831
• Page End: 2835
• Publication Date: 2018-06-17
• Subjects: asymmetric relay catalysis -- gold -- nickel -- cycloaddition -- fused bicyclic heterocycles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201800576
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An efficient catalytic asymmetric cyclization/inverse‐electron‐demand hetero‐Diels‐Alder cascade reaction of β, γ‐unsaturated α‐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. Abstract :