Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

Abstract

In this revision a summary of the trends of the formation of complex or not so complex heterocyclic structures through 1,3-DC of azomethine ylides is described. Diastereo-and enantioselective processes as well as nonasymmetric cycloadditions constitute very important synthetic tools for achieving all these series of compounds. The contents are classified as follows: 1. Introduction 2. Synthesis of spiroxindoles 3. Synthesis of spiropyrrolidines 4. Synthesis of spiropiperidines and piperidines 5. Synthesis of pyrrolidines and fused pyrrolidines 6. Synthesis of pyrrolizidines and indolizidines 7. Synthesis of quinolone and isoquinolines 8. Conclusions

Catalytic Enantioselective Formal Synthesis of MDM2 Antagonist RG7388 and Its Analogues

“…Chiral pyrrolidines are unparalleled and crucial structures that often appear in natural products, with unique biological activities and application values, which greatly enriched the scope of drug discovery . In recent years, some promising drug candidates with this skeletons were discovered (Figure ), for example, ABBV‐ 3221 is a modulator of the CFTR protein in development as a potential therapy for cystic fibrosis .…”

1,3‐Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst

“…[1,2] In addition, high stereospecificity, regio-, and diastereoselectivity are very frequently achieved due to the high control of the geometry of the dipole, as well as the preferential dipolarophile approach. [1,2] In addition, high stereospecificity, regio-, and diastereoselectivity are very frequently achieved due to the high control of the geometry of the dipole, as well as the preferential dipolarophile approach.…”

Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

“…In this context, various synthetic methods have been utilized for the chiral synthesis of spirocyclic pyrrolidine skeletons in recent years. Among most approaches, the 1,3-dipolar cycloaddition between azomethine ylides and electron-deficient alkenes is one of the most effective tools for building such skeletons with high to excellent endo/exo-diastereoand enantioselectivities [5][6][7][8]. Since the first asymmetric version of synthesis of spirooxindole-pyrrolidine derivatives was realized by Gong et al, via chiral BINOL-derived phosphoric acids, to catalyze the 1,3-dipolar cycloaddition of azomethine ylides formed in situ with N-Ac 2-oxoindolin-3-ylidenes [9].…”