Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Abstract

Catalytic asymmetric 1,3-dipolar cycloadditions of azomethine ylides have turned out to be one of the most efficient methods for the preparation of enantioenriched pyrrolidines. The past decade has witnessed the development of a bunch of well-defined catalytic systems capable of affording excellent diastereo and enantioselectivities. Recently, a great effort has been focused on expanding the scope of the cycloaddition with regard to both reaction partners. In this review,

The design, synthesis and application of imidazolium-tagged ferrocenyl oxazoline phosphine ligands for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes: ion effect for enhancing the reactivity, stereoselectivity and recyclability

“…14 Over the past few decades, some examples of the asymmetric 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles catalysed by chiral metal complexes and organocatalysts have been reported with excellent levels of stereoselectivity. 15 In particular, Hou et al 16a first reported switchable exo/endo selectivity in the 1,3-dipolar cycloaddition reaction of azomethine ylides with nitroalkenes. Later, Arai reported on the use of a PyBidineCu(OTf) 2 catalyst to synthesise endo-selective pyrrolidine products.…”

The Future of Catalysis by Chiral Lewis Acids

“…Others are relatively unstable and must be prepared in situ. Several recent reviews have focused on these increasingly popular reactions [18,[70][71][72]. Theoretical analyses have given significant insights into the controlling features of 1,3-dipolar cycloaddition reactions [73].…”

Highly Selective Copper‐Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Acyclic 1,3‐Dienes

“…[3] One of the most powerful approaches for the preparation of pyrrolidines is the 1,3-dipolar cycloaddition of azomethine ylides with activated olefins. [4] Over the course of the past decade, a great effort has been devoted to the development of catalytic systems based either on the use of different metal salts and chiral ligands [5] or organocatalysts. [6] With this set of outstanding systems, much interest has been recently devoted to expanding the scope of the cycloaddition to a wider variety of dipoles and dipolarophiles.…”