Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Abstract

The aim of this feature article is to show the stereochemical versatility of the metal-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Guided by evolution: from biology oriented synthesis to pseudo natural products

“…The 1,3-dipolar cycloaddition is a powerful method to introduce pyrrolidine moieties into scaffolds. [27][28][29] The development of regio-, diastereo-and enantioselective 1,3-dipolar cycloadditions makes it a versatile tool for synthesis. 27 Ningalin B and lamellarin D are two classes of marine natural products exhibiting interesting biological activities including antitumor activity, HIV-1 integrase inhibition and multidrug resistance reversal activity.…”

“…[27][28][29] The development of regio-, diastereo-and enantioselective 1,3-dipolar cycloadditions makes it a versatile tool for synthesis. 27 Ningalin B and lamellarin D are two classes of marine natural products exhibiting interesting biological activities including antitumor activity, HIV-1 integrase inhibition and multidrug resistance reversal activity. 30 The synthesis of the common pyrrolocoumarine core-scaffold was achieved through intramolecular 1,3dipolar cycloadditions from alkynes 13 (Scheme 5).…”

Synergistic Catalysis with Azomethine Ylides

“…[ 7 ] Although the asymmetric transformation of azomethine ylides has been extensively studied in the past thirty years, the reported examples mainly focused on the asymmetric 1,3‐dipolar [3+2] cycloadditions for the construction of pyrrolidine derivatives. [ 8 ] In a classical azomethine ylide‐involved asymmetric reaction, the chiral catalyst such as a Lewis acid (Cu, Ag, Ca, Ni, ··· complex) or a phase‐transfer catalyst was introduced solely to activate azomethine ylides and control the stereoselectivity. This single activation model requires the reaction partner to be highly activated dipolarophiles, such as electron‐deficient alkenes or imines (Scheme 1a).…”

Silver‐Catalyzed Diastereoselective Synthesis of Spirocyclic Pyrrolidine‐Lactones by 1,3‐Dipolar Cycloaddition

“…The 1,3‐dipolar cycloadditions (1,3‐DCs) involving intermediate azomethine ylides are one of the best processes employed by scientists, even by nature, to achieve these types of scaffolds . The asymmetric synthesis of the molecules containing this stereogenic quaternary center can be accessed in catalytic enantioselective processes or in diastereoselective routes using chiral auxiliaries attached to the substrates.…”