Synthesis of Spirocyclic Pyrrolidine Compounds via Silver-Catalyzed Asymmetric [3 + 2] Cycloaddition Reaction of Imino Esters with α-Alkylidene Succinimides
Ayana Inoue, Kenya Hosono, Shohei Furuya, Shin‐ichi Fukuzawa
Abstract
In this study, the AgOAc/ThioClickFerrophos (TCF) complex was used to successfully catalyze asymmetric [3 + 2] cycloaddition between glycine imino esters and CO 2 Me-appended α-alkylidene succinimides to afford spiropyrrolidines in good yields with high diastereo- and enantioselectivities (up to 95% ee). The silver/TCF afforded endo -(2,5- cis ) cycloadducts in contrast to the previous exo ′-(2,5- trans ) selective reaction with ylidene-2,3-dioxopyrrolidine. A wide variety of imino esters bearing electron-donating and electron-withdrawing groups on the phenyl groups and heteroaryl substrates were utilized in this reaction. The scope of α-alkylidene succinimides was investigated, which revealed that substituents on α-benzylidene derivatives had negligible effect on the product yield and stereoselectivity, and α-alkylidene derivatives could be efficiently used as dipolarophiles.