Catalytic Asymmetric Transformations of Racemic Aziridines

Abstract

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook

Recent Advances in (Dynamic) Kinetic Resolution and Desymmetrization Catalyzed by Chiral Phosphoric Acids

“…Epoxides [27] and aziridines [28] have been recognized as valuable intermediates in organic synthesis due to their ready availabilities and easy transformations. In 2016, List and co‐workers reported an efficient kinetic resolution of epoxides by CPA‐catalyzed thionation of epoxides (Scheme 18).…”

Recent Advances in Synthetic Strategies for the C4a,C9a-Fused Tetracyclic Hydrocarbazole Core Structure of Minfiensine and Related Akuammiline Alkaloids

“…Aziridine is a synthetically useful aminoethyl group equivalent, which is introduced by means of nucleophilic ring-opening reaction. [32][33][34] In 2015, Zhao and co-workers developed a formal [3+2] cycloaddition of indole with aziridines to construct tetracyclic hydrocarbazole (Scheme 7). 35 The formal 36 In this reaction, indole 45 was activated with triethylborane and potassium tert-butoxide, and the resulting borate 46 underwent nucleophilic addition at C3 with allylaziridine 47, followed by cyclization to furnish tetracyclic hydrocarbazole 48 in 38% yield with 2:1 dr.…”

(1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol

“…Aziridines are recurrent motifs in anticancer compounds (Figure 1A) and are useful building blocks in organic synthesis, largely due to their ring strain [1]. [2][3][4].…”

“…1 H NMR spectrum; FigureS2:13 C-NMR spectrum; Figure S3: HSQC spectrum; Figure S4: HRMS. Author Contributions: Conceptualization and supervision, F.S.…”